Deoxygenation of Alcohols via Acetates using Diphenylsilane

Abstract

The reaction of cyclododeey1 acetates derived from secondary alcohol, cyclododecanol, with 4 equivalents of diphenylsilane in the presence of 0.5 equivalent of di-t-butyl peroxide (DTBP) as a radical initiator gave cyclododecane. The reaction did not proceed without DTBP. The best results were obtained in the case of acetate as ester compared w ith the other esters such as isobutyrate, pivarate, or benzoate. Acetates derived from primary and tertiary alcohols were also deoxygenated, although the yields were relatively low. In the case of the deoxygenation of acetylated sugars, the yields were poor and a large amount of by-products were produced. It seems that the major factor is related to the fact that diphenylsilane has two reaction site and readily disproportionate to the other silanes.