Tetrahedron letters

A convenient coupling reaction of allyl alcohols with grignard reagents using 1-chloro-2-methyl-N, N-tetramethylenepropenylamine

T Fujisawa, S Iida, H Yukizaki, T Sato

Index: Fujisawa, Tamotsu; Iida, Sachio; Yukizaki, Hisashi; Sato, Toshio Tetrahedron Letters, 1983 , vol. 24, # 51 p. 5745 - 5748

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Citation Number: 14

Abstract

In the present reaction, although the reaction path via allyl chloride from allyl alcohol was presumable, the following fact seemed to exclude the formation of allyl chloride. The reaction of crotyl chloride with β-phenethylmagnesium bromide in the presence of HMPA and copper(I) iodide afforded a mixture of 3-methyl-5-phenyl-1-pentene and 6-phenyl-2-hexene in 85% yield in the ratio of 70:30, respectively, which was much inferior to the selectivity ...