Relative Reactivities of Various Sulfides, Selenides and Halides Towards SH2 Attack by Tributyltin Radicals

Athelstan L.J. Beckwith; Paul E. Pigou

doi:10.1071/CH9860077

Relative Reactivities of Various Sulfides, Selenides and Halides Towards S_H2 Attack by Tributyltin Radicals

Athelstan L.J. Beckwith, Paul E. Pigou

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Abstract

The order of reactivity towards S_H2 attack by tributyltin radicals on various groups X in four different molecular environments (RCO₂CH₂X, RCH₂OCH₂X, XCH₂CO₂Et and RCH₂X) has been found by competition experiments to be Br < PhSe < Cl < p-CNC6H4S < PhS < p- MeC₆H₄S < MeS. The mechanism of the reaction of chloromethyl phenyl sulfide with alkoxides is discussed.

Original language	English
Pages (from-to)	77-87
Number of pages	11
Journal	Australian Journal of Chemistry
Volume	39
Issue number	1
DOIs	https://doi.org/10.1071/CH9860077
Publication status	Published - 1986
Externally published	Yes

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abstract = "The order of reactivity towards SH2 attack by tributyltin radicals on various groups X in four different molecular environments (RCO2CH2X, RCH2OCH2X, XCH2CO2Et and RCH2X) has been found by competition experiments to be Br < PhSe < Cl < p-CNC6H4S < PhS < p- MeC6H4S < MeS. The mechanism of the reaction of chloromethyl phenyl sulfide with alkoxides is discussed.",

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AB - The order of reactivity towards SH2 attack by tributyltin radicals on various groups X in four different molecular environments (RCO2CH2X, RCH2OCH2X, XCH2CO2Et and RCH2X) has been found by competition experiments to be Br < PhSe < Cl < p-CNC6H4S < PhS < p- MeC6H4S < MeS. The mechanism of the reaction of chloromethyl phenyl sulfide with alkoxides is discussed.

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Relative Reactivities of Various Sulfides, Selenides and Halides Towards S_H2 Attack by Tributyltin Radicals

Abstract

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