ChemInform Abstract: Electrophilic Additions to Styrylsilanes: The Effect of Changing the Ligands on Silicon.

Abstract

Electrophilic Additions to Styrylsilanes: The Effect of Changing the Ligands on Silicon.-The products of the addition of carbon electrophiles and protons depend upon the nonparticipating substituents on silicon. (Ic) readily reacts with electrophiles. The reaction products do not contain silicon or new C-C bonds, protiodesilylation is favored. In contrast, ( Ia) does not participate in the reaction with carbon electrophiles or strong protic acids. However, with triflic acid (Ia) dimerizes. Under the same conditions (Ib) produces a different diastereoisomer together with a trimer. The reasons for the changes in the mechanism are discussed. -(BROOK, M. A.; HENRY, C.; JEFFERSON, E.; JUESCHKE, R.; SEBASTIAN, T.; TOMASZEWSKI, M.; WENZEL, S.; Bull. Soc. Chim. Fr. 132 (1995) 5-6, 559-568; Dep. Chem., McMaster Univ., Hamilton, Ont. L8S 4M1, Can.; EN)