Journal of the American Chemical Society

Allyl and benzyl migrations in the semibenzene rearrangement

B Miller, KH Lai

Index: Miller,B.; Lai,K.-H. Journal of the American Chemical Society, 1972 , vol. 94, # 10 p. 3472 - 3481

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Citation Number: 21

Abstract

Abstract: Allyl and benzyl groups migrate rapidly from C-4 to the exocyclic methylene group of cross-conjugated methylenecyclohexadienes. Rearrangement occurs rapidly at room temperature and below, except when the exocyclic methylene group is flanked by tert-butyl groups. Deuterium labeling studies show that the two ends of the allyl group become equivalent during the reaction. The rearrangement rates are variable, show significant ...