Intramolecular photocycloaddition reactions of 3-(2-propenoxy) cyclopent-2-en-1-ones and 3-(2-propenoxy) cyclohex-2-en-1-ones

…, BE Turk, DJ McGarvey, AA Manevich

Index: Matlin, Albert R.; Turk, Benjamin E.; McGarvey, David J.; Manevich, Alejandro A. Journal of Organic Chemistry, 1992 , vol. 57, # 17 p. 4632 - 4638

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Citation Number: 12

Abstract

The 3-oxa-1, 5-hexadienones 4a, 4b, 5a, and 5b undergo intramolecular [2+ 21 photocycloaddition reactions with quantum yields ranging from 0.2 to 0.002. In general, oxa substitution decreases the quantum yields and favors the formation of crossed cloeure producta in comparison to the alkenyl analogs. Irradiation of stereoe~ ically deuterated dienones lla and 12a indicate that the intermediate biradical reverts to the starting ...