Radical Addition of. ALPHA.-Halo Ester to Homoallylic Gallium or Indium Species: Formation of Cyclopropane Derivatives.

S Usugi, T Tsuritani, H Yorimitsu, H Shinokubo…

Index: Usugi, Shin-Ichi; Tsuritani, Takayuki; Yorimitsu, Hideki; Shinokubo, Hiroshi; Oshima, Koichiro Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 4 p. 841 - 845

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Citation Number: 16

Abstract

Treatment of benzyl bromoacetate with 3-butenylgallium dichloride in ether in the presence of a catalytic amount of Et 3 B as a radical initiator provided benzyl 3-cyclopropylpropanoate in 64% yield via a radical addition–substitution sequence. The use of 3-butenylindium dichloride in place of the gallium reagent also afforded the same product in good yield.