Rearrangements of organosilicon compounds I. The migratory aptitudes of various organic groups in the aluminum chloride-catalyzed rearrangement of (chloromethyl …

OW Steward, WJ Uhl, BW Sands

Index: Steward,O.W. et al. Journal of Organometallic Chemistry, 1968 , vol. 15, p. 329 - 337

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Citation Number: 22

Abstract

Abstract The migratory aptitudes of various organic groups in the aluminum chloride- catalyzed rearrangement of (chloromethyl) triorganosilanes have been determined: Me, 1.00; Et, 2.07; n-Pr, 2.97; iso-Pr,⪡ 1.00; ClCH 2,⪡ 1.00. Migration of the organic group from silicon to carbon is facilitated by electron-release and inhibited, relative to methyl, by branching at the α-carbon. The migratory aptitudes determined in this study and obtained ...