The invention of new radical chain reactions. Part XIII. Generation and reactivity of perfluoroalkyl radicals from thiohydroxamic esters

Derek H.R. Barton; Brigitte Lacher; Samir Z. Zard

doi:10.1016/S0040-4020(01)90613-1

The invention of new radical chain reactions. Part XIII. Generation and reactivity of perfluoroalkyl radicals from thiohydroxamic esters

Derek H.R. Barton
, Brigitte Lacher
, Samir Z. Zard

Centre national de la recherche scientifique

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

45 Citations (Scopus)

Abstract

The perfluoro acid esters of N-hydroxypyridine 2-thione give perfluoroalkyl radicals on irradiation. Without any trap the radicals participate in a decarboxylative rearrangement to give 2-perfluoroalkylthiopyridines in excellent yield. In the presence of an appropriate trap, such as an electron rich olefin, adducts are formed in variable yield.

Original language	English
Pages (from-to)	2325-2328
Number of pages	4
Journal	Tetrahedron
Volume	42
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4020(01)90613-1
Publication status	Published - 1 Jan 1986

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title = "The invention of new radical chain reactions. Part XIII. Generation and reactivity of perfluoroalkyl radicals from thiohydroxamic esters",

abstract = "The perfluoro acid esters of N-hydroxypyridine 2-thione give perfluoroalkyl radicals on irradiation. Without any trap the radicals participate in a decarboxylative rearrangement to give 2-perfluoroalkylthiopyridines in excellent yield. In the presence of an appropriate trap, such as an electron rich olefin, adducts are formed in variable yield.",

author = "Barton, \{Derek H.R.\} and Brigitte Lacher and Zard, \{Samir Z.\}",

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AU - Barton, Derek H.R.

AU - Lacher, Brigitte

AU - Zard, Samir Z.

PY - 1986/1/1

Y1 - 1986/1/1

N2 - The perfluoro acid esters of N-hydroxypyridine 2-thione give perfluoroalkyl radicals on irradiation. Without any trap the radicals participate in a decarboxylative rearrangement to give 2-perfluoroalkylthiopyridines in excellent yield. In the presence of an appropriate trap, such as an electron rich olefin, adducts are formed in variable yield.

AB - The perfluoro acid esters of N-hydroxypyridine 2-thione give perfluoroalkyl radicals on irradiation. Without any trap the radicals participate in a decarboxylative rearrangement to give 2-perfluoroalkylthiopyridines in excellent yield. In the presence of an appropriate trap, such as an electron rich olefin, adducts are formed in variable yield.

U2 - 10.1016/S0040-4020(01)90613-1

DO - 10.1016/S0040-4020(01)90613-1

M3 - Article

AN - SCOPUS:0011854291

SN - 0040-4020

VL - 42

SP - 2325

EP - 2328

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

The invention of new radical chain reactions. Part XIII. Generation and reactivity of perfluoroalkyl radicals from thiohydroxamic esters

Abstract

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