Studies on the Addition of Allyl Oxides to Sulfonylallenes. Preparation of Highly Substituted Allyl Vinyl Ethers for Carbanionic Claisen Rearrangements.

Scott E Denmark, Michael A. Harmata, Kathleen S. White

Research output: Contribution to journalArticlepeer-review

Abstract

Thirty-five allyl vinyl ethers bearing an arylsulfonyl anion-stabilizing group have been prepared by addition of allylic alkoxides to (arylsulfonyl)allenes. The allyl vinyl ethers are produced as either β,γ-unsaturated or α,β-unsaturated sulfones depending upon the substitution pattern of the allene and the reaction conditions. A wide variety of substitution patterns are available by using this method. Factors that control the position and stereochemistry of the vinyl ether double bond are discussed.

Original languageEnglish (US)
Pages (from-to)4031-4042
Number of pages12
JournalJournal of Organic Chemistry
Volume52
Issue number18
DOIs
StatePublished - Sep 1 1987

ASJC Scopus subject areas

  • Organic Chemistry

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