Evidence for Single Electron Transfer in the Reactions of Alkali Metal Amides and Alkoxides with Alkyl Halides and Polynuclear Hydrocarbons

Article abstract of DOI:10.1021/jo00324a056

Evidence for single electron transfer as the major pathway in reactions previously considered to be classic S_N1 and S_N2 pathways has been obtained.In this connection, the reaction of KOBu-t with trityl bromide has been shown to proceed through the trityl radical, and the reaction of LiN(i-Pr)2 with a primary alkyl iodide probe gave evidence of proceeding by single electron transfer, as indicated by the cyclized nature of the product as a result of a radical intermediate.