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- W2040246004 abstract "7,8-Dimethoxy-7,8-diphenyl- (1c), 7,8-dimethyl-7,8-diphenyl- (1d), 7-methoxy-7,8,8-triphenyl- (1e), 7-methyl-7,8,8-triphenyl- (1f), 7-isocyano-7,8,8-triphenyl- (1g), and 7,7,8-triphenylbenzocyclobutene (1h) are amenable to a variety of thermal rearrangements following initial electrocyclic ring-opening to the corresponding 7,8-diphenyl- (2c,d) and 7,8,8-triphenyl-o-quinodimethanes (2e–h). meso-1c was found to undergo a facile meso/rac isomerization at room temperature, indicating that other processes such as a symmetry-forbidden disrotatory ring-opening or a stepwise reaction compete with the symmetry-allowed conrotatory process. An estimate of the energy profile of the 1c/2c reaction system was made by kinetic simulation in combination with oxygen trapping of the intermediate o-quinodimethanes (2c) and semiempirical PM3 calculations, and revealed that the barrier for the symmetry-forbidden pathway is merely about 4 kJ·mol–1 higher than that for the symmetry-allowed one. o-Quinodimethanes 2c, 2g, 2e, and 2h underwent further electrocyclic hexatriene-cyclohexadiene ring-closure to give 4a,10-dihydroanthracene derivatives at temperatures between 20 and 80 °C. The 4a,10-dihydroanthracenes were further transformed to 9,10-disubstituted anthracenes by elimination of methanol or HCN, as well as to 9,10-substituted 9,10-dihydroanthracene derivatives. ESR and ENDOR spectroscopic detection of related 9-anthryl radicals lends support to the view that 9,10-dihydroanthracene products are formed by a homolytic hydrogen-transfer reaction (retrodisproportionation). By way of contrast, the aforementioned transformations play only a minor role in the case of methyl-substituted benzocyclobutenes 1d, 1f as here they are overruled by faster 1,5-H shift reactions of the corresponding o-quinodimethanes 2d, 2f, leading to styrene derivatives." @default.
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- W2040246004 date "1999-03-01" @default.
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- W2040246004 title "Thermal Rearrangements of Di- and Triphenyl-Substituted Benzocyclobutenes and Correspondingo-Quinodimethanes" @default.
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- W2040246004 doi "https://doi.org/10.1002/(sici)1099-0690(199903)1999:3<551::aid-ejoc551>3.0.co;2-2" @default.
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