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

Research output: Contribution to journalArticle

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
Publication statusPublished - Dec 27 1996

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Tin
Hydrides
Anions
Cations
Derivatives
Oxidation
Electrons
Electrooxidation
Cyclization
Cyclic voltammetry
triphenyltin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Tanaka, H., Ogawa, H., Suga, H., Torii, S., Jutand, A., Aziz, S., ... Amatore, C. (1996). Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions. Journal of Organic Chemistry, 61(26), 9402-9408.

Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions. / Tanaka, Hideo; Ogawa, Hidenori; Suga, Hiroaki; Torii, Sigeru; Jutand, Anny; Aziz, Said; Suarez, Alejandra G.; Amatore, Christian.

In: Journal of Organic Chemistry, Vol. 61, No. 26, 27.12.1996, p. 9402-9408.

Research output: Contribution to journalArticle

Tanaka, H, Ogawa, H, Suga, H, Torii, S, Jutand, A, Aziz, S, Suarez, AG & Amatore, C 1996, 'Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions', Journal of Organic Chemistry, vol. 61, no. 26, pp. 9402-9408.
Tanaka, Hideo ; Ogawa, Hidenori ; Suga, Hiroaki ; Torii, Sigeru ; Jutand, Anny ; Aziz, Said ; Suarez, Alejandra G. ; Amatore, Christian. / Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions. In: Journal of Organic Chemistry. 1996 ; Vol. 61, No. 26. pp. 9402-9408.
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AU - Aziz, Said

AU - Suarez, Alejandra G.

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