Chemoselective Isomerization of Secondary-Type Propargylic Alcohols to Propargylic/Allenic Bromides, and Brominated Dienes with Appel-Type Reaction Conditions

Norio Sakai*, Tsukasa Maruyama, Takeo Konakahara

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan, Email: sakachemrs.noda.tus.ac.jp

N. Sakai, T. Maruyama, T. Konakahara, Synlett, 2009, 2105-2106.

DOI: 10.1055/s-0029-1217701

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Abstract

A chemoselective isomerization of secondary-type propargylic alcohols under Appel-type reaction conditions in the presence of Ph₃P, CBr₄ and additives gives allenic bromides, propargylic bromides and brominated dienes.

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Key Words

Appel reaction, propargylic alcohol, allenes, dienes, isomerization, bromination

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ID: J60-Y2009-2380