Abstract
Abstract The titled compunds 1-exo-Cyano-1a,7b-dihydro-1H-cyclopropa[a]naphthalenes(8a), 1-endo-Cyano-1a,7b-dihydro-1H-cyclopropa[a]naphthalenes(8b), were photolyzed in several solvents. The results were: (1) The isomerization proceeded faster in aprotic nonpolar solvents than in polar ones. (2) The 1-endo derivative (8b) rearranged faster than the 1-exo-isomer (8a). (3) 8b was isomerized through Berson-Willcott rearrangement by the fission of bonds C1–C7b and C1–C1a, while 8a gave 1-cyanomethylnaphthalene (5b) as a main product. (4) Examination with an optically active 1-exo derivative (8a) showed that the exo-endo interconversion occured by the simultaneous two centered (30%) and one centered (70%) epimerization.
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