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 - Christl, Manfred
A1 - Brüntrup, Gisela
T1 - Diimine Reduction and Ozonolysis of Benzvalene
N2 - Via reduction of benzvalene (1) with diirnine tricyclo[3.1.0.02•6]hexane is obtained in good yield. The procedure renders 3, which has already been synthesized by Lemal and Shim, accessible much easier and in larger quantities. IH and 13C n.m.r. spectroscopic data are discussed. Both the thermal and the AgBF4-catalyzed rearrangernent of 3 yield 1,3-cyclohexadiene (8). - The ozonolysis of 1 with subsequent LiAIH4-reduction results in cis-I,3- bis(hydroxyrnethyl)cyclobutane (13a).
N2 - Durch Reduktion von Benzvalen (1) mit Diimin wird das Tricyc1o[3.1.0.02•6]hexan (3) in guter Ausbeute erhalten. Das Verfahren macht das bereits von Lemal und Shim dargestellte 3 erheblich leichter und in größeren Mengen zugänglich. IH- und 13C-NMR-spektroskopische Daten werden diskutiert. Sowohl die thermische als auch die AgBF4-katalysierte Umlagerung von 3 führt zu 1,3-Cyclohexadien (8). - Die Ozonolyse von 1 mit anschließender LiAlH4-Reduktion ergibt das cis-l,3-Bis(hydroxymethyl)cyclobutan (13a).
KW - Organische Chemie
Y1 - 1974
U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-57953
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 - 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 - 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 - 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 - 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 - 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 - 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 - 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 - 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 - 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 - 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-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 - 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[4.1.0.02.7]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 - 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[3.2.0.02
KW - 7]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 - 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 - 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 - 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 - 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 -