γ-Ray-induced reduction of sterically hindered alkyl carboxylates with trichlorosilane in the presence of hydrogen chloride. Two-step mechanism for the formation of alkanes via the alkyl chloride

Article abstract of DOI:10.1016/0022-328X(89)85276-3

γ-Irradiation of a mixture of 1-adamantyl acetate and trichlorosilane (TCS) in the presence of hydrogen chloride yields adamantane. The first step of this reaction entails cleavage of the alkyloxygen bond by the action of HCl and TCS to give the alkyl chloride. The chloride, in the second step, is dechlorinated by TCS by a known, free-radical mechanism. t-Amyl and benzyl acetates react analogously to 1-adamantyl acetate in this system to give isopentane and toluene, whereas other primary and secondary alkyl derivatives produce the corresponding dialkyl ethers by a known, free-radical mechanism.