Photochemistry of cyclopropene derivatives. 34. Photocycloaddition reactions of 2-alkenyl-substituted cyclopropenes

A Padwa, KE Krumpe, LW Terry…

Index: Padwa, Albert; Krumpe, Keith E.; Terry, Lenny W.; Wannamaker, M. Woods Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1635 - 1642

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Citation Number: 20

Abstract

The sensitized irradiation of 2-(4-pentenyl)-substituted cyclopropenes produces tricycle [3.3. 0.01* 3] octanes by means of a novel intramolecular [2+ 21 cycloaddition. In dramatic contrast to the photochemical results, thermolysis affords a product containing the bicyclo [4.1. O] heptane ring. The thermal reaction proceeds via ring opening of the cyclopropene to give a vinylcarbene, which subsequently adds across the neighboring a-bond. The ...