Rearrangements of organosilicon compounds I. The migratory aptitudes of various organic groups in the aluminum chloride-catalyzed rearrangement of (chloromethyl)triorganosilanes
作者:Omar W. Steward、William J. Uhl、Bruce W. Sands
DOI:10.1016/s0022-328x(00)91311-1
日期:1968.12
The migratoryaptitudes 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;ClCH2, ⪡ 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 migratoryaptitudes determined
Silicon-induced diastereoselectivity of the catalyzed phosphorylation of 1-(perfluoroalkyl)-ω (trialkylsilyl)alkan-1-ols
作者:G. N. Molchanova、T. M. Shcherbina、P. V. Petrovskii、I. Yu. Kudryavtsev、L. S. Zakharov
DOI:10.1007/s11172-005-0064-3
日期:2004.9
1-(perfluoroalkyl)-ω-(trialkylsilyl)alkan-1-ols with pentavalent phosphorus acid monochlorides (phosphonochloridates, methyl(phenyl)phosphinic chloride, and phosphorochloridates) was studied. The effects of the structures of alcohols and phosphorylatingagents on the degree of the reaction diastereoselectivity were investigated. Methylphosphonochloridates were found to react most stereoselectively; the diastereoselectivity