Regioselective synthesis of allyltrimethylsilanes from allylic halides and allylic sulfonates. Application to the synthesis of 2, 3-bis (trimethylsilyl) alk-1-enes

JG Smith, SE Drozda, SP Petraglia…

Index: Smith, Janice Gorzynski; Drozda, Susan E.; Petraglia, Susan P.; Quinn, Nina R.; Rice, Elizabeth M.; et al. Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4112 - 4120

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Citation Number: 63

Abstract

The preparation of allyltrimethylsilanes by regioselective pathways is described. Treatment of (E)-l-chloro-Zalkenes with a reagent prepared from 1 equiv each of trimethylsilyllithium and copper (1) iodide in hexamethylphosphoramide to presumably form a (trimethylsily1) copper reagent affords 3-(trimethylsilyl)-l-alkenes in good to excellent yields with high regioselectivity. Treatment of these same 1-chloro-2-alkenes with (trimethylsily1) lithium ...

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