Grignard coupling reaction of bis(chloromethyl)diorganosilanes with dichloro(diorgano)silanes: Syntheses of 1,3-disilacyclobutanes

Abstract

The Grignard coupling reaction of bis(chloromethyl)diorganosilanes [(ClCH(2))(2)SiR(1)R(2): R(1) = R(2) = Me, 1a; R(1) = Me, R(2) = Ph, 1b; R(1) = R(2) = Ph, 1c] with diorganodichlorosilanes [(Cl(2)SiR(3)R(4): R(3) = R(4) = Me, 2a; R(3) = Me, R(4) = Ph, 2b; R(3) = R(4) = Ph, 2c] at THE reflux temperature gave the intermolecular C-SI coupling product of 1,1,3,3-tetraorgano-1,3-disilacyclobutanes 3a-f in poor to moderate yields ranging from 7% to 50% along with polydiorganosilapropanes. The cyclization reaction of 1a-c with methyl-substituted dichlorosilanes 2a, b gave 1,3-disilacyclobutanes 3a-c, e, d in moderate yields (42-50%), while the same reaction with dichlorodiphenylsilane (2c) to 1,3-disilacyclobutanes 3d, f resulted in low yield (7-18%) probably due to the steric hindrance of two-phenyl groups on the silicon of 2c.