@article{LeiningerLanzendoerferChristl1983, author = {Leininger, H. and Lanzend{\"o}rfer, F. and Christl, Manfred}, title = {{\"U}ber die Reduktion des Benzvalenozonids zum cis-1,3-Cyclobutandimethanol mit LiAlH\(_4\)}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58130}, year = {1983}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlHerbert1979, author = {Christl, Manfred and Herbert, R.}, title = {Unusual Carbon Shielding Effects of Cyclopropanes and Double Bonds in Strained Bicyclo[3.1.0]hexanes and Cyclopentenes}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58038}, year = {1979}, abstract = {Carbon-13 shieldings and one-bond \(^{13}\)C-H coupling constants of bicydo[2.1.1]hexane, bicydo[2.l.l]hex- 2-ene, tricydo[3.1.1.0\(^{2.4}\)]heptane and benzvalene are presented and compared. to the data of related. compounds. H a bicydo[3.1.0]hexane system is part of a rigid skeleton, the cydopropane ring exerts spedfk: 'Y substituent eflects of two ldnds. In the case of the bicyclobexane boat form an upfield shift of the C-3 signal is observed and in tbe esse of the chair form a downfield shift of 15-20 ppm. Compared to the corresponding cydopentanes the double bond in strained cydopentenes causes downfield shifts of the C-4 absorption. 1bis eftect increases witb increasing strain, reaching 8 45.9 ppm maximum in benzvalene. Hence it is tbe only known bicydo[l.l.O]butane baving 8 reversed order of carbon shieldings. The downfield shifts are e:xplained by means of simple orbital interaction schemes.}, subject = {Organische Chemie}, language = {en} } @article{ChristlLang1982, author = {Christl, Manfred and Lang, R.}, title = {Tricyclo[5.1.0.0\(^{2,8}\)]octa-3,5-diene (Octavalene)}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58124}, year = {1982}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlKraft1988, author = {Christl, Manfred and Kraft, A.}, title = {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}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58462}, year = {1988}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlHeinemannKristof1975, author = {Christl, Manfred and Heinemann, U. and Kristof, W.}, title = {Thermal Rearrangement of Some Endo-Endo'-Bridged Bicyclo[1.1.0]butanes}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-57967}, year = {1975}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlLangHerzog1986, author = {Christl, Manfred and Lang, R. and Herzog, C.}, title = {The Synthesis of Octavalene (Tricyclo[5.1.0.0\(^{2,8}\)]octa-3,5-diene) and Several Substituted Octavalenes}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58254}, year = {1986}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlReuchlein1990, author = {Christl, Manfred and Reuchlein, H.}, title = {Synthesis and NMR Spectra of 2,3-Dihydro-1,3-methanoindene Derivatives and 1,2,3,5-Tetrahydro-1,3-methanopentalene}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58557}, year = {1990}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{MarkgrafCortDavisetal.1991, author = {Markgraf, J. H. and Cort, J. R. and Davis, H. A. and Lindeman, N. I. and Myers, C. R. and Kraft, A. and Christl, Manfred}, title = {Strained Heterocyclic Systems. 20. Basicities of Bicyclic Quinoxalines}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58584}, year = {1991}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{VolzShinPrinzbachetal.1978, author = {Volz, H. and Shin, J.-H. and Prinzbach, H. and Babsch, H. and Christl, Manfred}, title = {Stability of Tricyclo[4.1.0.0\(^{2,7}\)]heptenyl-Cations}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58001}, year = {1978}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{BentleyNormanGerstneretal.1993, author = {Bentley, T. W. and Norman, S. J. and Gerstner, E. and Kemmer, R. and Christl, Manfred}, title = {Solvolysis of Tricyclo[3.1.0.0\(^{2,6}\)]hex-3-yl and Bicyclo[2.1.1]hex-2-yl Sulfonates}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58689}, year = {1993}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlFreundHennebergeretal.1988, author = {Christl, Manfred and Freund, S. and Henneberger, H. and Kraft, A. and Hauck, J. and Irngartinger, H.}, title = {Several Polycyclic Valence Isomers of Dimethyl [14]Annulene-1,8-dicarboxylate. Reactivity of a "Nonconjugated" Bis(bicyclo[1.1.0]butane)}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58413}, year = {1988}, abstract = {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.}, subject = {Organische Chemie}, language = {en} } @article{KorthMuellerSustmannetal.1987, author = {Korth, H.-G. and M{\"u}ller, W. and Sustmann, R. and Christl, Manfred}, title = {Rearrangement of Free Radicals, XII. ESR Spectroscopic Study of the Ring Opening of the Homobenzvalenyl Radical}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58376}, year = {1987}, abstract = {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.}, subject = {Organische Chemie}, language = {en} } @article{ChristlBraun1989, author = {Christl, Manfred and Braun, Max}, title = {Photocycloadditions of Benzvalene}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58506}, year = {1989}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlTuerkPetersetal.1994, author = {Christl, Manfred and T{\"u}rk, M. and Peters, K. and Peters, E.-M. and Schnering, H. G. von}, title = {Octahydro-1,2,3:4,5,6-dimethenopentalene-2-carbonitrile, the First Derivative of a Yet-Unknown (CH)\(_{10}\)-Hydrocarbon}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58731}, year = {1994}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlReichRoberts1971, author = {Christl, Manfred and Reich, H. J. and Roberts, J. D.}, title = {Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Chemical Shifts of Methylcyclopentanes, Cyclopentanols, and Cyclopentyl Acetates}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-57862}, year = {1971}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{ChristlRoberts1972, author = {Christl, Manfred and Roberts, J. D.}, title = {Nuclear Magnetic Resonance Spectroscopy : Carbon-13 Chemical Shifts of Small Peptides as a Function of pH}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-57885}, year = {1972}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{BentleyChristlNorman1991, author = {Bentley, T. W. and Christl, Manfred and Norman, S. J.}, title = {Methanesulfonate/p-Nitrobenzoate and p-Toluenesulfonate/p-Nitrobenzoate Rate Ratios. Solvolyses of 1-Adamantyl and Benzhydryl Substrates}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58599}, year = {1991}, abstract = {No abstract available}, subject = {Organische Chemie}, language = {en} } @article{BentleyChristlKemmeretal.1994, author = {Bentley, T. W. and Christl, Manfred and Kemmer, R. and Llewellyn, G. and Oakley, J. E.}, title = {Kinetic and Spectroscopic Characterisation of Highly Reactive Methanesulfonates. Leaving Group Effects for Solvolyses and Comments on Geminal Electronic Effects Influencing S\(_N\)1 Reactivity}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58748}, year = {1994}, abstract = {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).}, subject = {Organische Chemie}, language = {en} } @article{ChristlBruentrup1974, author = {Christl, Manfred and Br{\"u}ntrup, Gisela}, title = {Diimine Reduction and Ozonolysis of Benzvalene}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-57953}, year = {1974}, abstract = {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).}, subject = {Organische Chemie}, language = {en} } @article{KimChristlKochl1990, author = {Kim, E. and Christl, Manfred and Kochl, J. K.}, title = {Charge-Transfer Cycloaddition of Homobenzvalene with Tetracyanoethylene}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-58537}, year = {1990}, abstract = {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.}, subject = {Organische Chemie}, language = {en} }