Chloranil-sensitized photolysis of benzyltrimethylsilanes. Solvent effect on the competition between carbon-hydrogen and carbon-silicon bond cleavage

E Baciocchi, T Del Giacco, F Elisei…

Index: Baciocchi, Enrico; Giacco, Tiziana Del; Elisei, Fausto; Ioele, Marcella Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7974 - 7983

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Citation Number: 27

Abstract

A steady state and laser flash photolysis study of the chloranil (CA)-sensitized oxidation of benzyltrimethylsilane (BTS) and (4-methoxybenzy1) trimethylsilane (MBTS) in different solvents (benzene, CH2C12, and MeCN) has been carried out. In benzene, BTS reacts with VA* to give exclusively a-substituted benzyltrimethylsilane, whereas with MBTS the a- substituted silane is formed together with benzylic desilylation products. The latter ...