Vinyl migration in Wittig rearrangements

V Rautenstrauch, G Buchi, H Wuest

Index: Rautenstrauch,V. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 2576 - 2580

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Citation Number: 34

Abstract

Abstract: Some allyl vinyl and benzyl vinyl ethers are transformed to lithium salts of divinylcarbinols and benzylvinylcarbinols, respectively, by the agency of butyllithium. The geometry of the migrating double bond is preserved in this new [1, 21 rearrangement. Metallation often is slower than rearrangement and alkylation prior to rearrangement is usually not feasible. Cleavage of an initially formed lithium species to a vinyllithium ...