TY  - JOUR
A1  - Christl, Manfred
A1  - Türk, M.
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Octahydro-1,2,3:4,5,6-dimethenopentalen-2-carbonitril, das erste Derivat eines noch unbekannten (CH)\(_{10}\)-Kohlenwasserstoffs
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58728
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Türk, M.
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Octahydro-1,2,3:4,5,6-dimethenopentalene-2-carbonitrile, the First Derivative of a Yet-Unknown (CH)\(_{10}\)-Hydrocarbon
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58731
ER  - 
TY  - JOUR
A1  - Bentley, T. W.
A1  - Christl, Manfred
A1  - Kemmer, R.
A1  - Llewellyn, G.
A1  - Oakley, J. E.
T1  - Kinetic and Spectroscopic Characterisation of Highly Reactive Methanesulfonates. Leaving Group Effects for Solvolyses and Comments on Geminal Electronic Effects Influencing S\(_N\)1 Reactivity
N2  - Highly reactive methanesulfonates (mesylates, ROMs) have been prepared from 1-phenylethanol. cyclohex-2-en-1-ol, diphenylmethanol and p-methoxybenzyl alcohol by treatment with methanesulfonyl chloride and triethylamine in dichloro- or trichloro-methane at - 20 to 0 °C. The mesylates. characterised in solution by \(^1\)H and \(^{13}\)C NMR at -20 °C, were obtained in satisfactory purity (ca. 95%) in cold solutions but they decomposed by reaction with chloride, triethylamine or the parent alcohol. Rate constants for solvolyses in aqueous acetone and aqueous ethanol have been determined by a fast response conductimetric method. Product selectivities for solvolyses of pmethoxybenzyl mesylate in aqueous ethanol and methanol at 0 °C have been determined by HPLC. From additional new or Iiterature kinetic data for solvolyses of corresponding bromides. chlorides and p-nitrobenzoates (OPNB). Br/CI. OMs/Br and OMs/OPNB rate ratios were calculated; the results are consistent with electronic effects stabilising the carbocationic transition states and increasing OMs/Br rate ratios for these SN 1 solvolyses; none of the evidence supports a geminal electronic effect on Br/CI rate ratios (e.g. caused by stabilisation of the initial state in pmethoxybenzyl chloride). Steric effects on ester /halide rate ratios for solvolyses of tertiary substrates are confirmed. Relative rates over a 10\(^{16}\) range for ester and halide leaving groups are evaluated for solvolyses of 1-phenylethyl substrates in 80% ethanol-water. updating previous work by Noyce et al. (1972).
KW  - Organische Chemie
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58748
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Gerstner, E.
A1  - Kemmer, R.
A1  - Llewellyn, G.
A1  - Bentley, T. W.
T1  - Elektrophile Additionen an das Bicyclo[1.1.0]butan-System von 1-Phenyl- und 1-(4-Anisyl)tricyclo[4.1.0.0\(^{2,7}\)]heptan: Säure-katalysierte Reaktionen mit Wasser und  Methanol, Anlagerung von Essigsäure und Oxymercurierung
N2  - No abstract available
KW  - Organische Chemie
KW  - 6-Norpinanols
KW  - 6-aryl-
KW  - preparation
KW  - 6-Norpinyl 3
KW  - 5-dinitrobenzoates
KW  - hydrolysis
KW  - Carbocations
KW  - generation and rearrangement
KW  - 2-Norcaranols
KW  - 1-aryl-
KW  - Cyclohept-3-en-1-ols
KW  - 3-aryl-
KW  - conformation
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58696
ER  - 
TY  - JOUR
A1  - Gerstner, E.
A1  - Kemmer, R.
A1  - Christl, Manfred
T1  - Elektrophile Additionen an das Bicyclo[1.1.0]butan-System von Tricyclo[4.1.0.0\(^{2,7}\)]-heptan-Derivaten: Halogen-Elektrophile
T1  - Electrophilic Additions to the Bicyclo[l.l.O)butane System of Tricyclo[4.1.0.0\(^{2,7}\)]heptane Derivatives: Halogen Electrophiles
N2  - No abstract available
KW  - Organische Chemie
KW  - Norpinanes
KW  - preparation
KW  - Carbocations
KW  - classical and nonclassical
KW  - Neighbouring group participation
KW  - Halonium ions
KW  - Migratory aptitudes in carbocations
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58700
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Martin
A1  - Wolz, E.
A1  - Wagner, W.
T1  - Cycloallene, 9 - 1-Phenyl-1-aza-3,4-cyclohexadien, das  erste Isodihydropyridin: Erzeugung und Abfangreaktionen
T1  - Cycloallenes, 9 - 1-Phenyl-1-aza-3,4-cyclohexadiene, the First Isodihydropyridine: Generation and Interception
N2  - No abstract available
KW  - Organische Chemie
KW  - Isoquinolines
KW  - hexahydro-
KW  - Cyclobuta[c}pyridines
KW  - hexahydro-
KW  - Cycloadditions
KW  - [2 + 2]- and [4 + 2]-
KW  - 3-Azabicyclo{3
KW  - 1
KW  - 0]hexane
KW  - 6
KW  - 6-dibromo-3-phenyl-
KW  - 2
KW  - 4-Pentadienylamine
KW  - 3-n-butyl-N-phenyl-
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58714
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Leß, Roland
A1  - Müller, Heinrich
T1  - 6,7-Dimethylene-2,4-diphenylbicyclo[3.2.l]oct-3-en-2-yl Anion : A Test for the Origin of the Unusual Properties of the Bicyclo[3.2.l]octa-3,6-dien-2-yl Anion
N2  - No abstract available
Y1  - 1994
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-31547
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Lanzendörfer, U.
A1  - Grötsch, M. M.
A1  - Hegmann, J.
A1  - Ditterich, E.
A1  - Hüttner, G.
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Cycloadditionen von 6H-1,3,4-0xadiazin-6-onen (4,5-Diaza-α-pyronen), 12 - Dieckmann-Kondensationen ohne Basen
T1  - Cycloadditions of 6H-1,3,4-0xadiazin-6-ones (4,5-Diaza-α-pyrones), 12 - Dieckmann Condensations without Bases
N2  - No abstract available
KW  - Organische Chemie
KW  - 1
KW  - 3
KW  - 4-0xadiazine-2-carboxylate
KW  - methyl 6-oxo-5-phenyl-
KW  - Diels-Alder reactions
KW  - Ketenes
KW  - y-oxo-
KW  - 1
KW  - 2-Cyclopentanedione derivatives
KW  - Adipic acid
KW  - substituted 2-oxo- dimethyl esters
Y1  - 1993
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58665
ER  - 
TY  - JOUR
A1  - Feineis, E.
A1  - Schwarz, H.
A1  - Hegmann, J.
A1  - Christl, Manfred
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Cycloadditionen von 6H-1,3,4-0xadiazin-6-onen (4,5-Diaza-α-pyronen), 13 - Diels-Alder-Reaktionen mit 6H-1,3,4-Oxadiazin-6-onen als Dienophil
T1  - Cycloaddltions of 6H-1,3,4-0xadiazin-6-ones (4,5-Diaza-α-pyrones), 13 - Diels-Alder Reactions wtth 6H-1,3,4-0xadiazin-6-ones as Dienophile
N2  - No abstract available
KW  - Organische Chemie
KW  - 6H-1
KW  - 3
KW  - 4-0xadiazin-6-ones
KW  - 1
KW  - 2-Bismethylenecyclohexane
KW  - Diels-Alder reactions
KW  - [1
KW  - 3
KW  - 4]0xadiazino[4
KW  - 5-b]isoquinolin-1-one derivatives
KW  - Bicyclo[2.1.l]hexan-5-one
KW  - highly substituted
Y1  - 1993
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58673
ER  - 
TY  - JOUR
A1  - Bentley, T. W.
A1  - Norman, S. J.
A1  - Gerstner, E.
A1  - Kemmer, R.
A1  - Christl, Manfred
T1  - Solvolysis of Tricyclo[3.1.0.0\(^{2,6}\)]hex-3-yl and Bicyclo[2.1.1]hex-2-yl Sulfonates
N2  - No abstract available
KW  - Organische Chemie
KW  - Bicyclo[1.1.0]butylcarbinyl sulfonates
KW  - solvolysis of
KW  - Cyclobutylcarbinyl sulfonates
KW  - Anchimeric assistance in solvolysis
KW  - Rearrangement of carbocations
KW  - Electron demand in ditosylates
Y1  - 1993
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58689
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Müller, H.
T1  - Induktiver Effekt, negative Hyperkonjugation und Gegenion sind nicht die Ursache der besonderen Eigenschaften des Bicyclo[3.2.1]octa-3,6-dien-2-yl-Anions. - Eine NMR-Studie mit phenylsubstituierten Modellen
T1  - Inductive Effect, Negative Hyperconjugation, and Gegenion do not Cause the Unusual Properties of the Bicyclo[3.2.1]octa-3,6-dien-2-yl Anion. An NMR Study with Phenyl-Substituted Models
N2  - No abstract available
KW  - Organische Chemie
KW  - Tricyclo[3.3.1.0 2
KW  - 4]non-7-en-6-ylpotassium
KW  - 6-phenyl
KW  - Homoaromaticity in carbanions
KW  - Bicyclo[3.2.1]oct-3-en-2-yl anions
KW  - phenyl-substituted
Y1  - 1993
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58655
ER  - 
TY  - JOUR
A1  - Stangl, R.
A1  - Jelinek-Fink, H.
A1  - Christl, Manfred
T1  - Darstellung phenylsubstituierter Derivate des Tricyclo[4.1.0.0\(^{2,7}\)]heptans und des 1,2,3,4-Tetrahydro-1,2,3-methenonaphthalins
N2  - No abstract available
KW  - Organische Chemie
KW  - Bicyclo[3.2.0.0<sup>2
KW  - 7</sup>]heptane derivatives
KW  - Norcaranes
KW  - 7
KW  - 7-dibromo
KW  - lH-Cyclopropa[a]naphthalenes
KW  - 1
KW  - 1-dibromo-1a
KW  - 2
KW  - 3
KW  - 7b-tetrahydro-
KW  - Carbene insertion
KW  - Bicyclo[1.1.0]butane derivatives
Y1  - 1992
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58610
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Stangl, R.
A1  - Jelinek-Fink, H.
T1  - Zur Kenntnis der thermischen Umlagerung des Bicyclo[1.1.0]butan-Systems. Eine kinetische Studie des Übergangs von Tricyclo[4.1.0.0\(^{2,7}\)]heptanen in Bicyclo[3.2.0]hept-6-ene
T1  - On the Thermal Rearrangement of the Bicyclo[1.1.0]butane System. A Kinetic Investigation of the Conversion of Tricyclo[4.1.0.0\(^{2,7}\)]heptanes into Bicyclo[3.2.0)hept-6-enes
N2  - No abstract available
KW  - Organische Chemie
KW  - 3-Methenonaphthalenes
KW  - 4-tetrahydro-
KW  - kinetics of thermolysis
KW  - Benzocycloheptene derivatives
KW  - Bicyclo[1.1.0]butanes
KW  - rearrangement
KW  - Tricyclo[4.1.0.0<sup>2.7</sup>]heptanes
KW  - kinetics of thermolysis
KW  - Bicyclo[3.2.0]hept-6-ene derivatives
Y1  - 1992
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58623
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Martin
A1  - Müller, Germar
T1  - 1,2,4-Cyclohexatriene, an Isobenzene, and Bicyclo[4.4.0)deca-1,3,5,7,8-pentaene, an Isonaphthalene: Generation and Trapping Reactions
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1992
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58639
ER  - 
TY  - JOUR
A1  - Hegmann, J.
A1  - Ditterich, E.
A1  - Hüttner, G.
A1  - Christl, Manfred
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - δ-Chlor-δ-lactone aus γ-Oxoketenen
N2  - No abstract available
KW  - Organische Chemie
KW  - 1
KW  - 3
KW  - 4-0xadiazine-2-carboxylate
KW  - methyl 6-oxo-5-phenyl-
KW  - Diels-Alder reactions
KW  - Ketenes
KW  - y-oxo-
KW  - δ-Lactones
KW  - δ-chloro-
KW  - β-Lactones
Y1  - 1992
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58649
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Martin
A1  - Müller, Germar
T1  - 1,2,4-Cyclohexatrien, ein Isobenzol, und Bicyclo[4.4.0]deca-1,3,5,7,8-pentaen, ein Isonaphthalin : Erzeugung und Abfangreaktionen
N2  - No abstract available
Y1  - 1992
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-30249
ER  - 
TY  - JOUR
A1  - Reuchlein, H.
A1  - Kraft, A.
A1  - Christl, Manfred
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Reaktionen von Bicyclo[2.1.1]hexenen mit 1,3,4-Oxadiazin-6-onen und dynamische Effekte einem in neungliedrigen, überbrückten, α,β-ungesättigten Enollacton
N2  - No abstract available
KW  - Organische Chemie
KW  - 1
KW  - 3
KW  - 4-0xadiazin-6-ones
KW  - Diels-Alder reactions
KW  - Enol Iactones
KW  - Lactone conformations
KW  - Line-shape analysis
Y1  - 1991
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58577
ER  - 
TY  - JOUR
A1  - Markgraf, J. H.
A1  - Cort, J. R.
A1  - Davis, H. A.
A1  - Lindeman, N. I.
A1  - Myers, C. R.
A1  - Kraft, A.
A1  - Christl, Manfred
T1  - Strained Heterocyclic Systems. 20. Basicities of Bicyclic Quinoxalines
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1991
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58584
ER  - 
TY  - JOUR
A1  - Bentley, T. W.
A1  - Christl, Manfred
A1  - Norman, S. J.
T1  - Methanesulfonate/p-Nitrobenzoate and p-Toluenesulfonate/p-Nitrobenzoate Rate Ratios. Solvolyses of 1-Adamantyl and Benzhydryl Substrates
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1991
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58599
ER  - 
TY  - JOUR
A1  - Jelinek-Fink, H.
A1  - Christl, Manfred
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Cycloallene, 7 : Ein Siebenringallen-Dimer: Darstellung aus einem 7,7-Dibromnorcaran-Derivat und Thermolyse
T1  - Cycloallenes, 7 : A Seven-Membered-Ring Allene Dimer: Preparation from a 7,7-Dibromonorcarane Derivative and Thermolysis
N2  - No abstract available
KW  - Organische Chemie
KW  - Bisbenzo[ 4
KW  - 5]cyclohepta[ 1
KW  - 2-α:2'
KW  - 1' -c]naphthalene
KW  - hexahydro-
KW  - 7-Norcaranylidene carbenoid
KW  - substituted
KW  - Cycloallene dimerization
KW  - Tetrakis(arylmethylene)ethane diradical
KW  - 1
KW  - 2-Bismethylenecyclobutanes
Y1  - 1991
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58603
ER  - 
TY  - JOUR
A1  - Gigstad, Kenneth M.
A1  - Ricci JR., John S.
A1  - Markgraf, J. Hodge
A1  - Christl, Manfred
A1  - Kraft, Arno
T1  - Strained Heterocyclic Systems : 18. Structure of 1,2,3-Methylidyne-2,3-dihydro-1H-cyclopenta[b]quinoxaline
N2  - No abstract available
Y1  - 1991
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-41645
SN  - 0108-2701
ER  - 
TY  - JOUR
A1  - Kim, E.
A1  - Christl, Manfred
A1  - Kochl, J. K.
T1  - Charge-Transfer Cycloaddition of Homobenzvalene with Tetracyanoethylene
N2  - The transient yellow color observed in the cycloaddition of homobenzvalene (HB) with tetracyanoethylene (TCNE) is associated with the charge-transfer complex [HB, TCNE). The deliberate photoexcitation of [HB,TCNE) affords a mixture of charge-transfer cycloadducts (1, 2, and 3) that differs from that obtained in thermal cycloaddition. The relationship of {HB t TCNE•) radical-ion pair (as the critical reactive intermediate in charge-transfer cycloaddition) to the activation process for thermal cycloaddition is discussed.
KW  - Organische Chemie
KW  - Electron transfer
KW  - photochemical
KW  - Radical-ion pair
KW  - Photochemistry
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58537
ER  - 
TY  - JOUR
A1  - Lang, R.
A1  - Herzog, C.
A1  - Stangl, R.
A1  - Brunn, E.
A1  - Braun, M.
A1  - Christl, Manfred
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Reaktionen von Homobenzvalenen mit 4-Phenyl-3H-1,2,4-triazol-3,5(4H)-dion, Tetracyanethylen, Chlorsulfonylisocyanat und Schwefeldioxid. Einige konzertierte 1,4-Additionen an eine Vinylcyclopropan-Einheit
T1  - Reactions of Homobenzvalenes wlth 4-Phenyl-3H-1,2,4-trlazole-3,5(4H)-dione, Tetracyanoethylene, Chlorosulfonyl  Isocyanate, and Sulfur Dioxide. Several Concerted 1,4-Additions to a Vinylcyclopropane Subunit
N2  - No abstract available
KW  - Organische Chemie
KW  - 6-Thiatricyclo[3.2.1.o 2.7 ]oct-3-ene 6
KW  - 6-dioxide
KW  - Homo Diels-Alder reactions
KW  - Cyclopropanetetracarbonitrile derivatives
KW  - Barbaralane derivatives
KW  - Urazoles
KW  - polycyclic
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58527
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Reuchlein, H.
T1  - Synthesis and NMR Spectra of 2,3-Dihydro-1,3-methanoindene Derivatives and 1,2,3,5-Tetrahydro-1,3-methanopentalene
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58557
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Lanzendörfer, U.
A1  - Grötsch, M. M.
A1  - Ditterich, E.
A1  - Hegmann, J.
T1  - Cycloadditionen von 1,3,4-0xadiazin-6-onen (4,5-Diaza-alpha-pyronen), 9 - 6-Oxo-5-phenyl-1,3,4-oxadiazin-2-carbonsäure-methylester - Synthese und Reaktionen mit Norbornen, Norbornadien, Cyclopropenen, Cyclobuten und Benzvalen
N2  - No abstract available
KW  - Organische Chemie
KW  - 1
KW  - 3
KW  - 4-0xadiazin-6-ones
KW  - Diels-Alder reactions
KW  - y-Oxoketenes
KW  - ß-Lactones
KW  - bicyclic
KW  - Enol Iactones
KW  - alpha
KW  - ß-unsaturated
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58569
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Reuchlein, H.
T1  - Synthesen und NMR-Spektren von 2,3-Dihydro-1,3-methanoindenderivaten und 1,2,3,5-Tetrahydro-1,3-methanopentalen
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58549
ER  - 
TY  - JOUR
A1  - Irngartinger, H.
A1  - Reimann, W.
A1  - Lang, R.
A1  - Christl, Manfred
T1  - Electron Density Distribution in a Bicyclo[l.l.0]butane
N2  - No abstract available
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-31576
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Krimm, Stefan
A1  - Kraft, Arno
T1  - Some Valenes of Benzannelated Five-Membered Heteroarenes - Synthesis and NMR Spectra
N2  - No abstract available
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-30026
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Krimm, Stefan
A1  - Kraft, Arno
T1  - Einige Valene von benzanellierten fünfgliedrigen Heteroarenen - Synthesen und NMR-Spektren
N2  - No abstract available
Y1  - 1990
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-31559
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Martin
T1  - Generation and interception of 1-OXA-2,3-Cyclohexadiene and 1,2,4-Cyclohexatriene
N2  - The cycloadducts 6 and 7 of tricyc1o[4.1.0.0 2 ,7)hepta- 3,4-diene (~) with styrene and 1,3-butadiene rearrange to unusual products on thermolysis, namely the cycloheptatriene derivatives ~ and 10. 1-0xa-3,4-cyclohexadiene (20) is generated smoothly from 6,6-dichloro-3-oxabicyclo[3.1.0]hexane (22) and n-butyllithium. 1-0xa-2,3-cyclohexadiene (11) is formed from 6-exo-bromo-6-endo-fluoro-2-oxabicyclo[ 3.1.0]hexane (30) and methyllithium. In the presence of activated olefins, this reaction provides an efficient route to 28 and 33 - 38, the trapping products of 21. Interestingly, [2+2]-cycloadditions do not take place at the same double bond of 21 as [4+2]-cycloadditions. The reactions of 1,3-cyclopentadiene and indene with bromofluorocarbene afford 6-exo-bromo-6-endo-fluorobicyclo[3.1.0]hex-2-ene (50) and its benzo derivative ~, respectively. On treatment of these compounds with methyl lithium in the presence of styrene, the interception products 53 and 47 of 1,2,4-cyc10- hexatriene (44) and its benzo derivative 43, respectively, are formed in good yields.
KW  - Chemie
Y1  - 1989
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-56566
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Brunn, E.
A1  - Roth, W. R.
A1  - Lennartz, H.-W.
T1  - 7-Methyl- and 7-Phenylcyclohepta-1,3,5-trienes from Benzvalene Via 3,3a,4,5,6,6a-Hexahydro-4,5,6-methenocyclopentapyrazoles and Tetracyclo[4.1.0.0\(^{2,4}\).0\(^{3,5}\)]heptanes
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1989
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58471
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Brunn, E.
A1  - Kraft, A.
A1  - Irngartinger, H.
A1  - Huber-Patz, U.
T1  - Nichtbindende Wechselwirkungen in zwei 7-Spirotetracyclo[4.1.0.0\(^{2,4}\).0\(^{3,5}\)]heptanen
T1  - Nonbonded Interactions in two 7-Spirotetracyclo[4.1.0.0\(^{2,4}\).0\(^{3,5}\)]beptanes
N2  - Die Reaktion von Tetrachlordiazocyclopentadien mit Be.nzvalen (2) ergab das Fulven-Derivat 3. Dagegen führten die Umsetzungen von Diazoßuoren und 5-Diazo-10,1 1-dihydro-SH-dibenzo[ a.d]cyclohepten mit 2 zu den erwarteten Spiro-1-pyrazolinen 4 bzw. 5. Die photolytische Abspaltung von Stickstoff aus 4 und 5 lieferte die Spirotetracycloheptane 6 bzw. 7. Die Röntgenstrukturanalyse von 6 beweist einen engen Kontakt zwischen je eineßl Wasserstoffatom der Tetracycloheptan- und der Fluoren-Einheit. Dieser kurze Abstand (2.15 A) ruft Winkelaufweitungen hervor und wird auch als Grund für starke Entschirmungen der betreffenden Protonen und eine formal über sieben Bindungen reichende 0.6-Hz-Kopplung zwischen ihnen angesehen. 7 ist das erste chiralc Tetracyclohcptan. Ursache dafür ist eine nichtebene Konformation des Siebenrings, der bei Raumtemperatur nicht invertiert. Auf der Basis von NOE-Messungen gelang die Zuordnung der tH-NMR-Signale von 6 und 7.
N2  - The reaction or tctrachlorodiazocyclopentadiene with benzvalene (2) gavc, the fulvene derivative 3. In contrast, treatment of diazoßuorene and 5-diazo-1 0,1 1-dihydro·SH -dibenzo[ a,d]cycloheptene with l:afl'orded the expected spiro-1-pyrazolines 4 and 5, respectively. Photolytic extrusion of nitrogen from 4 and S led to the corresponding spirotetracyclobeptanes 6 and 7. The X-ray structure analysis of 6 revealed a close contact between one hydrogen atom cach of the tetracycloheptane and the ßuorene subunits. This short distance (2.15 A) causes an increase in bond angles and is believed to produce strong deshielding of the respective protons and a 0.6-Hz coupling between them, which is formally a long-range coupling across seven bonds. Compound 7 is the first chirat tetracycloheptane. This is due to a nonplanar confonnation of the seven-membered ring, which does not invert at room temperature. On tbe basis of NOE measurements the 1H-NMR signals of 6 and 7 are assigned.
KW  - Organische Chemie
KW  - 5H-Dibenzo[a
KW  - d]cycloheptene
KW  - 10
KW  - 11-dihydro- / 1-Pyrazoline
KW  - Nonbonded Interactions
KW  - Spirotetracyclo[4.1.0.0<sup>2
KW  - 4</sup>.0<sup>3
KW  - 5</sup>]beptanes
KW  - Long-range coupling constants
KW  - mtrogen extruston
Y1  - 1989
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58489
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Max
T1  - Photocycloadditionen des Benzvalens
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1989
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58492
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Max
T1  - Photocycloadditions of Benzvalene
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1989
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58506
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Braun, Martin
T1  - Freisetzung und Abfangreaktionen von 1-Oxa-2,3-cyclohexadien
T1  - Generation and Interception of 1-0xa-2,3-cyclohexadiene
N2  - Umsetzung von 6,6-Dichlor-2-oxabicyclo[3.1.0)hexan (4a) in Styrol mit n-Butyllithium lieferte neben Polystyrol und t-Chlor-1- pbenylhexan (6) in geringer Ausbeute die Tet~hydrocyclobutapyrane 5, die Abfangprodukte des aus 4a generierten t-Oxa-2,3- cyclobexadiens (3). Das unbeständige 6,6-Dibrom-2-oxabicyclo( J.l.O]hexan (4b) wurde bei -60°C erzeugt un~ bei -30°C mit Methyllithium in Gegenwart von Styrol umgesetzt, woraus die Produkte 5 mit 24% Ausbeute hervorgingen. Als bei 20°C beständige Quelle für 3 erwies sich exo-6-Brom-e~o-6-fluor-2-oxabicyclo[ J.t.O]bexan (9), das aus 2,3-Dihydrofuran und Bromßuorcarben mit 25% Ausbeute bereitet wurde. Behandlung von 9 in Styrol, <X-Methylstyrol, 1,3-Butadien, 2,3-Dimet~yl-!,3-butadien, Furan und 2,5-Dimethylfuran mit Methyllithium ergab Abfangprodukte von 3 mit Ausbeuten von 31-80%. Dabei entstanden mit den Styrolen und überwiegend auch mit den l ,3-Butadienen (2 + 2]-Cycloaddukte als Diastereomerengemische, nämlich 5, ll, 13 und 15. Die Furane lieferten ausschließlieb [4 + 2]-Cycloaddukte (17 und 18), die 1,3-Butadiene nur mit einem kleinen Anteil (14 und 16). [2 + 2]- und [4 + 2]-Cycloadditionen zeigen eine unterschiedliche Chemoselektivität. Während erstere die Enolether- Doppelbindung von 3 nutzen, finden letztere an der vom Sauerstoffatom entfernteren Doppelbindung statt. Das als 1 : IGemisch aus exo- und endo-Isomeren anfallende Produkt 5 lieferte beim Erhitzen auf l50°C ein 20:1: 1-Gemiseh aus exo- und endo-5 sowie dem Strukturisomeren 19. Thermolyse· des 2: 1-Gemisches aus 13 und 14 erbrachte ein 2: 1-Gemiscb aus 14 und dem Tetrahydro-1-benzopyran 20.
N2  - The reaction of 6,6-dichJoro-2-oxabicyclo[3.1.0]hexane (4a) in styrene with n-butylJithium gave. mainly polystyrene and 1- chloro-l-phenylhexane (6) but aft'orded the tetrahydrocyclobutapyrans 5, the trapping products of l-oxa-2,3-cyclohexadiene (3) generated froni 4a, only in Jow yield. The unstable 6,6-dibromobicyclo[ 3.1.0]hexane (4b) was generated at -60°C and treated witb methyllithium at -30°C in tbe presence ofstyrene providing the products 5 in 24% yield. Prepared from 2,3-dihydrofuran and bromofluorocarbene in 25% yield, exo-6-bromo-endo-6-ßuoro-2- oxabicyclo[J.t .O]hexane (9) is a stable source for 3. Thus, treatment of9 in styrene, <X-methylstyrene, 1,3-butadiene, 2,3-dimethyl- 1,3-butadiene, furan, and 2,5-dimethylfuran with methyllithium furnished interception products of 3 in 3!-80% yield. [2 + 2] Cycloadducts, i. e. 5, 12, 13, and 15, were fo!l"ed as mixtures or diastereomers with the styrenes and as main products also with the 1,3-butadienes. The furans gave [4 + 2] cycloadducts exclusively (17 and 18), the 1,3-butadienes only to a minor extent (14 and 16). [2 + 2] and [ 4 + 2] Cycloadditions display different chemoselectivity. Wbereas the former utilize the enol ether double· bond, the Iatter take place at tbe double bond more remote from the oxygen. Formed from 3 as a 1: t mixture of diastereomers, the product S gave a 20: 1: 1 mixture of exo-5, endo-5, and the structural isomer 19 on heating at 150°C. Thermolysis of the l: 1 mixture of 13 and 14 furnished a 2:1 mixture of 14 and tbe tetrabydro- 1-benzopyran 20.
KW  - Organische Chemie
KW  - 4
KW  - 4a
KW  - 5
KW  - 8-Tetrahydro-3H-2-benzopyrans
KW  - 3
KW  - 5
KW  - 8
KW  - 8a-Tetrahydro-2H-1-benzopyran
KW  - Allenes
KW  - six-membered
KW  - cyclic / 1-0xa-2
KW  - 3-cyclohexadiene
KW  - 3
KW  - 5
KW  - 6
KW  - 6a-Tetrahydro-2H-cyclobuta[b]pyrans
Y1  - 1989
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58517
ER  - 
TY  - JOUR
A1  - Hegmann, Joachim
A1  - Christl, Manfred
A1  - Peters, Karl
A1  - Peters, Eva-Maria
A1  - Schnering, Hans Georg von
T1  - Die Reaktionskaskade von 6-Oxo-5-phenyl-1,3,4-oxadiazin-2-carbonsäure-methylester und 1,3-Butadienen zu konjugierten und nichtkonjugierten Cyclopentenonen
N2  - Fünfgliedrige Carbocyclen sind Bauelemente zahlreicher NaturstofTe und daher attraktive Syntheseziele. Da bisher kein Syntheseverfahren mit großer Anwendungsbreite bekannt ist, sind neue Methoden willkommen. Wir berichten hier über Umsetzungen des Titelheterocyclus 1 mit l,3-Butadienen 1; diese Reaktionen, obwohl vielstufig, liefern im Eintopfverfahren konjugierte und nichtkonjugierte Cyclopentenone und gestatten auch die Fünfringanellierung.
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58421
ER  - 
TY  - JOUR
A1  - Freund, S.
A1  - Henneberger, H.
A1  - Christl, Manfred
T1  - Halbkäfigverbindungen aus Diels-Alder-Addukten des Benzvalens mit Cyclopentadien-Derivaten durch Radikalreaktionen mit Thiophenol und Bromtrichlormethan
T1  - Half-Cage Compounds by Radical Reactions with Thiophenol and Bromotrichloromethane from Diels-Alder Adducts of Benzvalene with Cyclopentadiene Derivatives
N2  - In Diels-Alder-Reaktionen wurden aus Benzvalen (1) und Tetrachlorcyclopentadienon- dimethylacetal sowie Tetrachlorfuran die Addukte 2 bzw. 8 und 9 erhalten. Behandlung von 2 mit Natrium und tert-Butylalkohol ergab das chlorfreie Acetal 3, dessen Doppelbindung sich mit Diimin unter Bildung von 4 absättigen ließ. Aus dem bekannten Stammkohlenwasserstoff 5 ging analog 6 hervor, und durch Reaktion seines Anions mit Chlorameisensäure- methylester entstand der Ester 7. - Die Verbindungen l, 3, 5, 7-9 und das bekannte U wurden mit Thiophenol so behandelt, daß Radikalkettenreaktionen abliefen. Bei 8 trat Addition an die Zentralbindung des Bicyclobutan-Systems ein. Dagegen unterlag bei 2, 9, U und zum Teil bei 3, deren Doppelbindung jeweils der BicycJobutan-Einheit benachbart ist, das Primärradikal der 5-Hexen-1-yl- Cyclopentylrneth.yl-Umlagerung, aus der letztlich 15, ll, 13 bzw. 16 resultierten. Zum Teil bei 3 und vollständig bei 5 erfolgte die Addition an die Doppelbindung zu 17 bzw. 18, d.h. ohne Beteiligung der benachbarten Bicyclobutan- Einheit. Durch Aktivierung des Bicyclobutan-Systems mit einer Esterfunktion konnte dessen Passivität aufgehoben werden. So entstanden aus 7 das nichtumgelagerte Produkt 19 und das umgelagerte 20. Ihr Verhältnis hing von der Konzentration an Thiophenol ab. - Analog zur Reaktion 1Z + Thiophenol-13 brachte BromtrichJormethan aus 12 das umlagerte Addukt 21 hervor. - Als Nebenprodukt wurde bei der Umsetzung von 12 mit Thiophenol das Chlorwasserstoff-Addukt 14 des ersteren gefunden. Modellreaktionen für die Bildung von 14 sind die Umsetzungen von 12 mit Essigsäure und von 3 sowie 5 mit +Nitrobenzoesäure zu den Addukten 22, 23 bzw. 24. Seit
N2  - The adducts 2, 8,. and 9 were obtained by Diels-Aider reactions of benzvalene (I) with tetrachlorocyclopentadienone dimethyl acetal and tetracblorofuran. respectively. On treatment of 2 with sodium and tert-butyl alcohol, the chlorine atoms were substituted by hydrogen atoms to give acetal 3, the double bond of · whicb could be hydrogenated by diimine with formation of 4. Analogously, the known parent hydrocarbon 5 afforded 6. Tbe anion of 5 reacted with methyl chloroformate to give the ester 7. - Compounds 2, 3, 5, 7-9, and the known 12 were treated with thiophenol under conditions causing radical chain reactions. Whereas 8 added the reagent across the centrat bond of the bicyclobutane system, the additions to 2, 9, 12 and in part to 3, the double bond of which is adjaceot to the bicyclobutane moiety in each case, were accompanied by a 5-hexen-1-yJcylcopentylmethyl rearrangement of the primary radical resulting in formation of 15, 11, 13, and 16, respectively. In part with 3 and completely with 5, the addition took place at the double bond to give 17 and 18, respectively, i.e. without involvement of the adjacent bicylcobutane moiety. Activation of the bicyclobutane system with an ester functionality led to its participation. Thus, compound 7 gave the nonrearranged product 19 and the rearranged one 20 with their ratio being dependent on the concentration of thiophenol. - In analogy to the reaction 12 + thiophenol-13, tbe rearranged adduct 21 was formed from 12 and bromotrichloromethane. - The hydrogen cbloride adduct 14 was found as a byproduct on treatment of 1l witb thiophenol. Model reactions for the formation of 14 are the additions of acetic acid to 12 an~ 4-nitrobenzoic acid to 3 and 5 leading to the adducts 22, 23, and 24, respectively.
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58435
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Henneberger, H.
A1  - Freund, S.
T1  - Halbkäfigverbindungen aus Polycyclen mit einem Bicyclo[1.1.0]butan-System und dazu benachbarter Azobrücke durch Radikalreaktionen mit Thiophenol und Bromtrichlormethan
T1  - Half-Cage Compounds by Radical Reactions with Thiophenol and Bromotrchloromethane from Polycyclic Compounds with a Bicyclo[1.1.0]butane System and an Adjacent Azo Bridge
N2  - Aus Benzvalen (J) und 3,6-Bis(2-pyridyl)-l,2,4,5-tetrazin wurde das Dihydropyridazin 2c erhalten, das ebenso wie die bekannten Dihydropyridazine 2a, b mit Cyclopropen in die entsprechende Azoverbindung 3 überging. Addition von Thiophenol an 3a, c und 5 lieferte unter Beteiligung des Bicyclobutan-Systems und der Azofunktion die Halbkäfigverbindungen 4a, c bzw. 6. Aus der Umsetzung von 7, in dem die Azobrücke durch zwei BicycJobutan- Systeme flankiert ist, mit Thiophenol sowie Bromtrichlormethan gingen die Halbkäfigverbindungen 8 bzw. 9 hervor. An diesen ~eaktionen wirken beide Bicyclobutan-Systeme und die Azofunktion mit.
N2  - Dihydropyridazine 2c was obtained from benzvalene (1) and 3,6- bis(2-pyridyJ)-1,2,4,5-tetrazine. Like the known dihydropyridazines 2a, b. compound 2c was converted into the corresponding azo compound 3 by treatment with cyclopropene. The addition of thiophenol to 3a, c and S yielded the half-cage compounds 4a, c and 6, respectively. In these processes the bicyclobutane system and the azo functionality are involved. Treatment of 7, in which the azo bridge has two bicyclobutane neighbours, with thiophenol and bromotrichloromethane led to the formation of the half-cage compounds 8 and 9, ~spectively. Both the bicyclobuta_ne systems and the azo functionality are transformed in these reactions.
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58440
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Kraft, A.
T1  - Tricyclo[3.1.1.0\(^{2,6}\)]hexandion (das Valen des o-Benzochinons), Bicyclo[2.1.1]hexan-2,3-dion und Valene eines Chinoxalins, des Phenazins sowie eines Benzophenazins
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58459
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Kraft, A.
T1  - Tricyclo[3.1.1.0\(^{2,6}\)]hexandion (the Valen of o-Benzochinons), Bicyclo[2.1.1]hexan-2,3-dion and Valene of a Chinoxalins, of Phenazins and of a Benzophenazine
N2  - No abstract available
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58462
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Freund, S.
A1  - Henneberger, H.
A1  - Kraft, A.
A1  - Hauck, J.
A1  - Irngartinger, H.
T1  - Several Polycyclic Valence Isomers of Dimethyl [14]Annulene-1,8-dicarboxylate. Reactivity of a "Nonconjugated" Bis(bicyclo[1.1.0]butane)
N2  - Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (5) with benzvalene (4), norbornene, and norbornadiene afforded the azo compounds 7 and 8. Theseare derivatives of 2,3-diazabicyclo[2.2.2]oct-2-ene as is azo compound 3, which had been obtained previously from 5 and 2 equiv of benzvalene (4). The photochemical extrusion of nitrogen from 3, 7, and 8 has been studied. Whereas 7 and 8 on direct irradiation in benzene gave rise exclusively to the bicyclo[2.2.0]hexane derivatives 9 and 10, respectively, from 3 in addition to the bicyclo[2.2.0]hexane 11, the diolefin 1l was formed. Diolefin 12 has cisdouble bonds in the nine-membered ring and is fixed in a boat conformation in a manner so that the two bicyclobutane systems approach each other very closely. This geometry suggests the unusual ring opening of the intermediate 1,4-cyclohexanediyl diradical from a boat conformation, which arises by inversion of the primarily generated boat conformation. Sensitized photolysis of 3 as weilasthat of ll produced the saturated isomer 13 of 11 and 12. The proximity of the bicyclobutane systems in 1l causes unprecedented reactions leading to cage compounds. When ll was heated at 90 °C, a rearrangement to the pentacyclic product 10 took place. Utilization of tetradeuteriated substrate ll-d4 supported a pathway with two diradical intermediates. Behaving in a convcntional manncr, bicyclobutane 9 and bis(bicyclobutane) 11 took up 1 and 2 equiv of thiophenol most probably in a radical-chain addition to give the thioethers 28 and 19, respectively. In contrast, bis(bicyclobutane) ll was converted by 1 equiv of thiophenol into cagc compound 30 in a process involving both the strained a systems. Heating at 80 °C subjected 30 to a reversible Copc rearrangement, resulting in a 6:1 mixture of 31 and 30. When it was treated with bromine, 11 was transformed to cage compound 38. This addition is believed to proceed via a cationic intermediate. The structure of cage compound 10 was established by a singlc-crystal X-ray analysis of dialcohol 11 prepared from 20 and methyllithium.
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58413
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Nusser, R.
A1  - Herzog, C.
T1  - 4-Bromoctavalen und zwei (Brommethylen)homobenzvalene anstelle eines erwarteten Bromoctabisvalens
N2  - No abstract available.
KW  - Organische Chemie
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58409
ER  - 
TY  - JOUR
A1  - Hegmann, Joachim
A1  - Christl, Manfred
A1  - Peters, Karl
A1  - Peters, Eva-Maria
A1  - Schnering, Hans Georg
T1  - Conjugated and Nonconjugated Cyclopentenones by a Reaction Cascade from Methyl 6-0xo-5-phenyl-1,3,4-oxadiazine-2-carboxylate and 1,3-Butadienes
N2  - No abstract available
Y1  - 1988
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-30207
ER  - 
TY  - JOUR
A1  - Schreck, Michael
A1  - Christl, Manfred
T1  - Generation and Interception of 1-Oxa-3,4-cyclohexadiene
N2  - No abstract available
KW  - Chemie
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-31601
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Schreck, Michael
T1  - 1,2,3,5,8,8a-Hexahydronaphthalin aus 1,2-Cyclohexadien
N2  - Reaktionen von 1,3-Butadien und einigen seiner Methylderivate mit 1a und 1- Methyl-1,2-cyclohexadien 1b sowie den Übergang der [2 + 2]-Cycloaddukte 2 und 3 in das bisher unbekannte 1,2,3,5,8,8a-HexahydronaphthaJin 4a und einige seiner Methylderivate
KW  - Chemie
KW  - Butadien
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-31656
ER  - 
TY  - JOUR
A1  - Schreck, Michael
A1  - Christl, Manfred
T1  - Freisetzung und Abfangreaktionen von 1-Oxa-3,4-cyclohexadien
N2  - No abstract available
KW  - Chemie
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-31597
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Herzog, C.
T1  - 3-(Phenylsulfonyl)tricyclo[4.1.0.0\(^{2,7}\)]hept-4-en-3-yllithium
N2  - Phenyl(tricyclo[4.1.0.0\^(^{2,7}\)] hept-4-en-3-yl)sulfone 8 has been prepared in two steps from 4,S-dlbromohomobenzvalene (6) and deprotonated to give the title compound 9. The carbon-13 NMR spectrum of 9 reveals a considerable interaction between the allyl anion moiety and the bicyclobutane system.
KW  - Organische Chemie
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58340
ER  - 
TY  - JOUR
A1  - Christl, Manfred
A1  - Schreck, M.
T1  - 7-Arylbicyclo[4.2.0]oct-1-ene - Synthese durch [2+2]-Cycloadditionen von 1,2-Cyclohexadien sowie 1-Methyl-1,2-cyclohexadien und thermische Äquilibrierung der exo/endo-Isomeren
T1  - 7-Arylbicyclo[4.2.0]oct-1-eaes - Synthesis by [2+2]Cycloadditions of 1,2-Cyclohexadiene and 1-Methyl-l,l-cyclohexadiene and Thermal Equilibration of the exo/endo Isomers
N2  - Das exo/endo--lsomerenverhältnis Ja: Jb bei der bekannten [2 + 2]-Cycloaddition von Styrol an 1,2-Cyclohexadien (2) wurde als tempcraturabhingiaaefunden. Der Einsatz von (Z)-Dcutcriostyrollicfene den Beweis der Zweistufiakeit dieser Reaktion, und das Diradikal 4 wird als wahrscheinlichste Zwischenstufe anaesehen. Erhitzen von Jb auf 140-170°C führte zur Binstellung des thermodynamischen Gleichgewichts mit Ja (Ja:3b = 93:7), wobei wieder das Diradikal4 als Zwischenstufe fungieren dürfte. Mit Hilfe kinetischer Messungen ermittelte man die Aktivierungsparameter für das System Ja~ 3b. - Aus 2 und den Abfangreagenzien p-Methoxystyrol, 1,1-Diphenylethylen sowie 1-Phenylpropen gingen mit bescheidenen Ausbeuten die Titelverbindungen 6a, b, 7 bzw. 8 hervor. Analoa zu 2 wurde sein l-Methylderivat 13 aus 6,6-Dibrom-1-methylbicyclo[3.1.0]hexan (9) durch Methyllithium freigesetzt. In Gegenwart von Styrol entstand neben den Abfanaprodukten 14a, b auch das Dimere 12 von lJ. - Die 1H-NMR-Spektren der Titelverbindungen belegen eine starre Halbsesselkonformation des Cyclohexentcils mit äquatorial anellienem Cyclobutanring.
N2  - The exofendo ratio of tbe isomers 3a, b formed in the kuown [2 + 2] cycloaddition of styrene to 1 ,2-cyclohexadiene (2) has been found to depend on the tempcrature. The utilization of (Z)deuteriostyrene provided the proof of the stepwise nature of this reaction with thc diradical 4 as the most probable intennediatc. Heating of 3b at l40-170°C established the thermodynamic equilibrium between Ja and Jb (3a:3b = 93:7) and again 4 is assumed to be the intermediatc. By means of kinetic measurements the activation parameten ofthe system 3a ~ Jb have been detcrmined. - From 2 and the trapping reagents p-metboxystyrene, 1,1-diphenylethylene, and 1-phenylpropene the title compounds 6a, b, 7, and 8, respectively, were formed in low yields. In analogy to 2 its 1-methyl derivative 13 has been generated from 6,6-dibromo-l-methylbicyclo[3.t.O]hexane (9) with methyUithium. From the reaction in the presence of styrcne the trappina products 14a, b were isolated in addition to the dimer ll of 13. - The 1H NMR spectra of the title compounds support a rigid halfchair conformation of the cyclohexene moiety with the cyclobutane ring ancllatcd equatorially.
KW  - Organische Chemie
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58352
ER  - 
TY  - JOUR
A1  - Korth, H.-G.
A1  - Müller, W.
A1  - Sustmann, R.
A1  - Christl, Manfred
T1  - Rearrangement of Free Radicals, XII. ESR Spectroscopic Study of the Ring Opening of the Homobenzvalenyl Radical
N2  - Abstraction of an allylic hydrogen atom in homobenzvalene (4) either in solurion by photolyticaßy generated tert-butoxyl radicals or in an adamantane matrix by X-rays produces the homobcnzvalenyl radical (5). which tbennally rearranps · to tbe tropylium ndical (1). In solution tbe activation cnergy for the rate determined step of the reaction sequence was detennined· to be 13.4 ± O.S kcal/mol.
KW  - Organische Chemie
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58376
ER  - 
TY  - JOUR
A1  - Hegmann, J.
A1  - Christl, Manfred
A1  - Peters, K.
A1  - Peters, E.-M.
A1  - Schnering, H. G. von
T1  - Intramolekulare [2+2]-Cycloadditionen von γ-Oxoketenen
N2  - The 1-oxoketenes, which are accessible from methyl 1,3,4-oxadiazin-6-one-2-carboxyIate 1 and cycloalkenes, are shown to undergo an intramolecular [2+2] cycloaddition either on heating or on photolysis to give different sterecisemers of ß-lactones of the 3-oxo-2-oxabicyclo[ 2.2.0]hexane-type.
KW  - Organische Chemie
Y1  - 1987
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-58384
ER  -