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

doi:10.1021/jo960741b

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

Faculty of Engineering

Research output: Contribution to journal › Article › peer-review

11 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 language	English
Pages (from-to)	9402-9408
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	61
Issue number	26
DOIs	https://doi.org/10.1021/jo960741b
Publication status	Published - Dec 27 1996

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo960741b

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

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.",

author = "Hideo Tanaka and Hidenori Ogawa and Hiroaki Suga and Sigeru Torii and Anny Jutand and Said Aziz and Suarez, {Alejandra G.} and Christian Amatore",

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doi = "10.1021/jo960741b",

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T1 - Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions

AU - Tanaka, Hideo

AU - Ogawa, Hidenori

AU - Suga, Hiroaki

AU - Torii, Sigeru

AU - Jutand, Anny

AU - Aziz, Said

AU - Suarez, Alejandra G.

AU - Amatore, Christian

PY - 1996/12/27

Y1 - 1996/12/27

N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

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

Abstract

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