Radical cyclisation reactions involving phosphonyl radicals: the use of phosphites and phosphine oxides as alternatives to tributyltin hydride

J M  Barks; B C  Gilbert; A F  Parsons; B  Upeandran

Radical cyclisation reactions involving phosphonyl radicals: the use of phosphites and phosphine oxides as alternatives to tributyltin hydride

J M Barks, B C Gilbert, A F Parsons, B Upeandran

Chemistry

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

Abstract

Free radical cyclisation of a variety of 1,6-dienes using CCl4 in the presence of diethyl phosphite or diphenylphosphine oxide has been investigated. These reactions involve addition of the trichloromethyl radical to the diene followed by a 5-exo-trig cyclisation reaction. The resultant cyclic primary radical can abstract a chlorine atom from CCl4 or alternatively, abstract a hydrogen atom from the solvent or the organophosphorus compound. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	3137-3140
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	17
Publication status	Published - 23 Apr 2001

Keywords

cyclisation
phosphorus compounds
radicals and radical reactions
LASER FLASH-PHOTOLYSIS
TIME-RESOLVED ESR
CYCLIZATION
REACTIVITY

Cite this

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title = "Radical cyclisation reactions involving phosphonyl radicals: the use of phosphites and phosphine oxides as alternatives to tributyltin hydride",

abstract = "Free radical cyclisation of a variety of 1,6-dienes using CCl4 in the presence of diethyl phosphite or diphenylphosphine oxide has been investigated. These reactions involve addition of the trichloromethyl radical to the diene followed by a 5-exo-trig cyclisation reaction. The resultant cyclic primary radical can abstract a chlorine atom from CCl4 or alternatively, abstract a hydrogen atom from the solvent or the organophosphorus compound. (C) 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "cyclisation, phosphorus compounds, radicals and radical reactions, LASER FLASH-PHOTOLYSIS, TIME-RESOLVED ESR, CYCLIZATION, REACTIVITY",

author = "Barks, {J M} and Gilbert, {B C} and Parsons, {A F} and B Upeandran",

year = "2001",

month = apr,

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language = "English",

volume = "42",

pages = "3137--3140",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Radical cyclisation reactions involving phosphonyl radicals: the use of phosphites and phosphine oxides as alternatives to tributyltin hydride

AU - Barks, J M

AU - Gilbert, B C

AU - Parsons, A F

AU - Upeandran, B

PY - 2001/4/23

Y1 - 2001/4/23

N2 - Free radical cyclisation of a variety of 1,6-dienes using CCl4 in the presence of diethyl phosphite or diphenylphosphine oxide has been investigated. These reactions involve addition of the trichloromethyl radical to the diene followed by a 5-exo-trig cyclisation reaction. The resultant cyclic primary radical can abstract a chlorine atom from CCl4 or alternatively, abstract a hydrogen atom from the solvent or the organophosphorus compound. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - Free radical cyclisation of a variety of 1,6-dienes using CCl4 in the presence of diethyl phosphite or diphenylphosphine oxide has been investigated. These reactions involve addition of the trichloromethyl radical to the diene followed by a 5-exo-trig cyclisation reaction. The resultant cyclic primary radical can abstract a chlorine atom from CCl4 or alternatively, abstract a hydrogen atom from the solvent or the organophosphorus compound. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - cyclisation

KW - phosphorus compounds

KW - radicals and radical reactions

KW - LASER FLASH-PHOTOLYSIS

KW - TIME-RESOLVED ESR

KW - CYCLIZATION

KW - REACTIVITY

M3 - Article

SN - 0040-4039

VL - 42

SP - 3137

EP - 3140

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -