The Journal of Organic Chemistry

Carbanion-accelerated Claisen rearrangements. 7. Phosphine oxide and phosphonate anion stabilizing groups

SE Denmark, JE Marlin

Index: Denmark, Scott E.; Marlin, John E. Journal of Organic Chemistry, 1991 , vol. 56, # 3 p. 1003 - 1013

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Citation Number: 36

Abstract

The utility of phosphine oxide and phosphonate groups has been examined in the context of the carbanionaccelerated Claisen rearrangement (CACR). Both of the groups permit the construction of substituted allyl vinyl ethers by allyl oxide addition to phosphorus-substituted allenes. Extensive optimization was required to suppress isomerization of both the allenes and the vinyl ethers. Using potassium dimsylate and lithium chloride as the base, both the ...