Control of regioselectivity in the di-. pi.-methane rearrangements. Triplet-sensitized photoisomerization of benzonorbornadienes carrying cyano substituents in the aryl …

LA Paquette, AY Ku, C Santiago…

Index: Paquette,L.A. et al. Journal of the American Chemical Society, 1979 , vol. 101, # 20 p. 5972 - 5980

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Citation Number: 13

Abstract

Abstract: Triplet-sensitized irradiation of 2-cyanobenzonorbornadiene (10) gives rise exclusively to 3-cyanotetracy-do [5.4. 0.02. 4.03, 6] undeca-1 (7), 8, 10-triene (30). This strong preference for benzo-vinyl bridging to C3 has also been observed in the case of the four possible aryl-substituted dicyano derivatives. In all of these examples, striking regiospecificity is exhibited, despite untoward aryl polar effects in two examples. This ...