Synthesis of the benzotricyclooctane ring system. Intramolecular [2+ 2] cycloaddition of indene derivatives

A Padwa, S Goldstein, M Pulwer

Index: Padwa, Albert; Goldstein, Steven; Pulwer, Mitchell Journal of Organic Chemistry, 1982 , vol. 47, # 20 p. 3893 - 3902

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Citation Number: 8

Abstract

The photosensitized triplet reactions of several 1-allyl-substituted indenes have been studied. The tripletsensitized irradiations gave benzotricyclo [3.3. 0.0 z~ 7] octanes in good yield by means of a novel intramolecular [2+ 21 cycloaddition. The effect of substituents on the regioselectivity of the sensitized rearrangement was studied in some detail. With the simple 1-allyl-substituted isomer, 1, 5-cyclization of the excited state is the preferred path. ...

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