Evidence for a di-π-methane rearrangement in the photoisomerization of 2, 3-benzo-7, 8-dimethylbicyclo [4.2. 0] octa-2, 4, 7-triene to 6, 7-dimethylbenzotricyclo …

CO Bender, IM Cassis, D Dolman…

Index: Bender, Christopher Owen; Cassis, Irene Marie; Dolman, Douglas; Heerze, Louis Dennis; Schultz, Frances Linda Canadian Journal of Chemistry, 1984 , vol. 62, p. 2769 - 2776

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Citation Number: 12

Abstract

Results 2, 3-Benzo-7, 8-dimethylbicyclo [4.2. 0] octa-2, 4, 7-triene (7) was conveniently prepared from the photolysis of 6, 7-dimethylbenzocyclooctatetraene (COT 9) by a modification of the previous method (1). The use of 1-acetonaphthone as sensitizer, instead of chlorobenzene, gave 7 in almost quantitative yield (Scheme 2). Compound 7 was less successfully prepared from the direct irradiation (Pyrex filter) of COT 9 due to secondary ...