Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions

Hideo Tanaka, Hidenori Ogawa, Hiroaki Suga, Sigeru Torii, Anny Jutand, Said Aziz, Alejandra G. Suarez, Christian Amatore

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10 Citations (Scopus)

Abstract

In our research of precursors of tin radicals able to initiate radical chain reactions under mild conditions, a series of triphenyltin derivatives Ph3SnY (Y = H, I, Cl, OTf, OCHO, SnPh3, SPh) is investigated by cyclic voltammetry. The results show that the tin radical Ph3Sn. is only produced from two compounds: by a one-electron oxidation of Ph3SnH or by a one-electron reduction of Ph3-SnI. Therefore electrooxidation of Ph3SnH generates Ph3Sn. which is able to initiate cyclization of haloalkynes. Reduction or oxidation of the other derivatives affords respectively the anion Ph3Sn- or the cation Ph3Sn+ because they are generated at potentials where the radical Ph3Sn. is either reduced or oxidized.

Original languageEnglish
Pages (from-to)9402-9408
Number of pages7
JournalJournal of Organic Chemistry
Volume61
Issue number26
DOIs
Publication statusPublished - Dec 27 1996

ASJC Scopus subject areas

  • Organic Chemistry

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