R. N. Depriest

Evidence for a single electron transfer mechanism in reactions of lithium diorganocuprates with organic halides

Abstract It has been demonstrated by means of spectroscopic studies involving cyclizable alkyl halides that lithium dimethylcuprate can react with organic halides by a single electron transfer pathway.

EPR evidence for a single electron transfer mechanism in reactions of aromatic ketones with lithium amides

Abstract Direct spectroscopic evidence (EPR) supporting a single electron transfer mechanism in the reaction of lithium amides with aromatic ketones is presented.

The first reported evidence of single electron transfer in the 1,2-addition of primary Grignard reagents to ketones☆

Abstract The first evidence to support the electron transfer nature of the reaction of primary Grignard reagents with aromatic ketones is presented.

Electron transfer in the reduction of primary halides by metal hydrides

Abstract The reactions of various main-group metal hydrides with 1-halo-5-hexenes and with 1-halo-2,2-dlmethyl-5-hexenes produce both straight chain and cyclized reduction products. The formation of cyclic hydrocarbons clearly indicates the presence of radical intermediates during the course of these reactions.

Spectroscopic evidence for the reduction of alkyl halides by metal hydrides via a single electron transfer mechanism

Abstract This report provides spectroscopic evidence to support a single electron transfer pathway to describe the reaction of metal hydrides with alkyl halides by direct EPR observation of the radical formed in the reaction.

Concerning the reduction of alkyl halides by LiAlH4 evidence that AlH3 produced in situ is the one electron transfer agent.

Abstract The reduction of 1° and 2° alkyl iodides by LiAlH 4 has been shown to involve a radical intermediate formed by the reaction of the alkyl iodide with the AlH 3 and LiI produced in situ in conjunction with LiAlH 4 rather than by LiAlH 4 alone, as evidenced by cyclized products in the reduction of 6-iodo-1-heptene, by the trapping of the radical and by stereochemical studies of the 2-halooctanes.

Evidence for single electron transfer in the reaction of alkoxides with alkyl halides

Abstract Evidence for a radical process in the reaction of lithium alkoxides with alkyl iodides was obtained by the observation of cyclization of appropriate radical probes, by the trapping of radicals, and by EPR spectroscopic observations relating to the one electron donor properties of alkoxides.