Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems

Ruben Maidan; Zafrir Goren; Itamar Willner; Janies Y. Becker

doi:10.1021/ja00333a017

Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems

Ruben Maidan
, Zafrir Goren
, Itamar Willner
, Janies Y. Becker

Institute of Chemistry

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

80 Scopus citations

Abstract

Photochemical and chemical reduction of N,N′-dioctyl-4,4′-bipyridinium (C₈V²⁺, 1) to the corresponding radical cation C₈V⁺· (2) leads to an induced disproportionation of C₈V⁺· in a water-organic two-phase system. This process yields the two-electron reduction product N,N′-dioctyl-4,4′(1H,1H′)-bipyridylidene (C₈V, 3). The induced disproportionation reaction is a result of opposite solubility properties of the disproportionation products in the two phases. The two-electron reduction product C₈V (3) mediates the debromination of 1,2- and 1,1-dibromo substrates.

Original language	English
Pages (from-to)	6217-6222
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	106
Issue number	21
DOIs	https://doi.org/10.1021/ja00333a017
State	Published - 1984

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title = "Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems",

abstract = "Photochemical and chemical reduction of N,N′-dioctyl-4,4′-bipyridinium (C8V2+, 1) to the corresponding radical cation C8V+· (2) leads to an induced disproportionation of C8V+· in a water-organic two-phase system. This process yields the two-electron reduction product N,N′-dioctyl-4,4′(1H,1H′)-bipyridylidene (C8V, 3). The induced disproportionation reaction is a result of opposite solubility properties of the disproportionation products in the two phases. The two-electron reduction product C8V (3) mediates the debromination of 1,2- and 1,1-dibromo substrates.",

author = "Ruben Maidan and Zafrir Goren and Itamar Willner and Becker, \{Janies Y.\}",

year = "1984",

doi = "10.1021/ja00333a017",

language = "אנגלית",

volume = "106",

pages = "6217--6222",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "21",

}

Maidan, R, Goren, Z, Willner, I & Becker, JY 1984, 'Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems', Journal of the American Chemical Society, vol. 106, no. 21, pp. 6217-6222. https://doi.org/10.1021/ja00333a017

Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems. / Maidan, Ruben; Goren, Zafrir; Willner, Itamar et al.
In: Journal of the American Chemical Society, Vol. 106, No. 21, 1984, p. 6217-6222.

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

TY - JOUR

T1 - Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems

AU - Maidan, Ruben

AU - Goren, Zafrir

AU - Willner, Itamar

AU - Becker, Janies Y.

PY - 1984

Y1 - 1984

N2 - Photochemical and chemical reduction of N,N′-dioctyl-4,4′-bipyridinium (C8V2+, 1) to the corresponding radical cation C8V+· (2) leads to an induced disproportionation of C8V+· in a water-organic two-phase system. This process yields the two-electron reduction product N,N′-dioctyl-4,4′(1H,1H′)-bipyridylidene (C8V, 3). The induced disproportionation reaction is a result of opposite solubility properties of the disproportionation products in the two phases. The two-electron reduction product C8V (3) mediates the debromination of 1,2- and 1,1-dibromo substrates.

AB - Photochemical and chemical reduction of N,N′-dioctyl-4,4′-bipyridinium (C8V2+, 1) to the corresponding radical cation C8V+· (2) leads to an induced disproportionation of C8V+· in a water-organic two-phase system. This process yields the two-electron reduction product N,N′-dioctyl-4,4′(1H,1H′)-bipyridylidene (C8V, 3). The induced disproportionation reaction is a result of opposite solubility properties of the disproportionation products in the two phases. The two-electron reduction product C8V (3) mediates the debromination of 1,2- and 1,1-dibromo substrates.

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Application of Multielectron Charge Relays in Chemical and Photochemical Debromination Processes. The Role of Induced Disproportionation of N,N′-Dioctyl-4,4′-bipyridinium Radical Cation in Two-Phase Systems

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