Journal of Organic Chemistry p. 662 - 666 (1992)
Update date:2022-08-11
Topics:
Tanner, Dennis D.
Chen, Jian Jeffrey
The reduction of α-haloacetophenones and α-halopropiophenones by 1,3-dimethyl-2-phenylbenzimidazoline (DMBI) have been reported to proceed via an electron-transfer free-radical chain mechanism.The reduction of α-haloisobutyrophenones did not proceed by the chain sequence.We mow report that initiated reductions of α-bromo- and α-chloroisobutyrophenones (IIIa,b) have been found to be promoted by the addition of thiophenol.Isobutyrophenone was formed as the major product via a free-radical chain process.During the PhSH-promoted DMBI reduction of IIIa,b a minor product, α-(phenylthio)isobutyrophenone (IV), was also formed via nucleophilic substitution.The chain propagation steps involve the efficient hydrogen atom transfers between PhCOCMe2. and PhSH and between PhS. and DMBI.The facile hydrogen transfer between PhS. and DMBI was comfirmed by carrying out the radical-chain reduction of PhSSPh with DMBI.
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