Photocycloaddition chemistry of 2-(trimethylsilyl) cyclopentenone and 5-(trimethylsilyl) uracil. The utility of a trimethylsilyl group as a removable directing group in …

C Shih, EL Fritzen, JS Swenton

Index: Shih, Chuan; Fritzen, Edward L.; Swenton, John S. Journal of Organic Chemistry, 1980 , vol. 45, # 22 p. 4462 - 4471

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Citation Number: 46

Abstract

The photocycloaddition reactions of 2-(trimethylsily1) cyclopentenone with isobutylene, methylenecyclohexane, isopropenyl acetate, propylene, and propyne were investigated. In the first three cases, a regiospecific reaction giving the head-to-tail photoadduct was observed while with propylene and propyne a mixture of head-to-head and head-tu-tail isomen was produced. The directing effect of the 5-trimethylsilyl group in uracil ...