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• W2007131944 abstract "Die 8-endo-Arylbicyclo[5.1.0]octa-2,4-diene 7a–e — durch Cycloaddition entsprechender Carbene (9a–e) an 1,3,5-Cycloheptatrien synthetisiert — isomerisieren bei etwa 130°C zu den benzokondensierten Tricyclen 12a–e. Bromaddition (Bildung von 13), 1H-NMR-spektroskopische Daten sowie die exemplarische Rontgenstrukturanalyse von 12b bestatigen die Umlagerungsreaktion. Sie kann als Carbo-Claisen-Umlagerung mit anschliesender 1,5-Homodienyl-Wasserstoffverschiebung (7 19 12) gedeutet werden. Ob die Isomerisierung 7 19 synchron oder uber das Diradikal 20 ablauft, kann vorerst nicht definitiv entschieden werden, jedoch scheint der Zweistufenmechanismus wahrscheinlicher zu sein. — Das 8-exo-Phenylbicyclo[5.1.0]octa-2,4-dien 8a geht erst bei 180°C Epimerisierung an C-8 sowie Fragmentierung zu Benzol und 14 ein, wobei offenbar die Zwischenstufen 21, 22 und 23 durchlaufen werden. Diese Reaktion ist nicht an die Anwesenheit eines Phenylrestes an C-8 gebunden.Carbenes, 17: Thermal Isomerization of 8-Phenylbicyclo[5.1.0]octa-2,4-dienesThe 8-endo-arylbicyclo[5.1.0]octa-2,4-dienes 7a–e — synthesized by cycloaddition reaction of the corresponding carbenes (9a–e) to 1,3,5-cycloheptatriene — isomerize at about 130°C to the benzo-condensed tricycles 12a–e. Addition of bromine (formation of 13), 1H NMR spectroscopic data as well as the exemplary X-ray crystal structure analysis of 12b confirm the rearrangement reaction. The reaction may be interpreted as a Carbo-Claisen-rearrangement followed by an 1,5-homodienyl hydrogen shift (7 19 12). Whether the isomerization 7 19 follows the synchronous way or takes the route via the diradical 20 cannot be decided for the present time, but the two-step mechanism seems to be more likely. — The 8-endo-phenylbicyclo[5.1.0]octa-2,4-diene 8a epimerizes at C-8 and fragments into benzene and 14 not below 180°C, 21, 22, and 23 apparently being the intermediates. This reaction does not depend on the presence of a phenyl group at C-8." @default.
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• W2007131944 title "Carbene, 17: Die thermische Isomerisierung von 8-Phenylbicyclo[5.1.0]octa-2,4-dienen" @default.
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• W2007131944 doi "https://doi.org/10.1002/cber.19781110509" @default.
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