Radical-initiated reduction of chloroformates to alkanes by tri-n-propylsilane. A method for removal of unwanted hydroxy-groups from organic molecules

Abstract

Chloroformates of primary and secondary alcohols, produced by the reaction of the alcohol with phosgene, are reduced to the corresponding alkane in excellent yields by reaction with tri-n-propylsilane in the presence of t-butyl peroxide at 140 °C. Unusually large amounts of initiator are required [0.5–1.1 mol (Bu^tO)₂ per mol of RO·CO·Cl]. The results are rationalized in terms of a free-radical reaction scheme.