Bulletin of the Chemical Society of Japan

Photo-induced polar addition of protic solvents to cycloalkenones. Evidence for the ground-state trans isomers as chemically-reactive intermediates

R Noyori, M Katô

Index: Noyori,R.; Kato,M. Bulletin of the Chemical Society of Japan, 1974 , vol. 47, p. 1460 - 1466

Full Text: HTML

Citation Number: 26

Abstract

The photo-induced reaction of cyclic α, β-unsaturated ketones with protic media is described. The irradiation of 2-cycloheptenone or 2-cyclooctenone in various protic solvents (alcohols, acetic acid, water, and diethylamine) results in the formation of Michael-type solvent adducts. The chemically-reactive species have been demonstrated to be the highly strained trans isomers in a ground state. The irradiation of cis-2-cyclononenone affords ...