New insight into the mechanism of the reaction between α,β-unsaturated carbonyl compounds and triethylborane (Brown's reaction)

Valérie Beraud; Yves Gnanou; John C. Walton; Bernard Maillard

doi:10.1016/S0040-4039(99)02279-0

New insight into the mechanism of the reaction between α,β-unsaturated carbonyl compounds and triethylborane (Brown's reaction)

Valérie Beraud, Yves Gnanou, John C. Walton, Bernard Maillard^*

^*Corresponding author for this work

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

36 Scopus citations

Abstract

A study of the reaction of α,β-unsaturated carbonyl compounds with triethylborane under free radical conditions (Brown's reaction) including spectroscopic analyses (¹¹B NMR, IR, EPR) of products and intermediates indicated that these reactions involve the prior formation of an 'α,β- unsaturated carbonyl compound-organoborane' complex. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	1195-1198
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(99)02279-0
State	Published - Feb 19 2000
Externally published	Yes

Keywords

Boron and compounds
Carbonyl compounds
Complexation
Enones
Radicals and radical reactions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)02279-0

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AU - Beraud, Valérie

AU - Gnanou, Yves

AU - Walton, John C.

AU - Maillard, Bernard

PY - 2000/2/19

Y1 - 2000/2/19

N2 - A study of the reaction of α,β-unsaturated carbonyl compounds with triethylborane under free radical conditions (Brown's reaction) including spectroscopic analyses (11B NMR, IR, EPR) of products and intermediates indicated that these reactions involve the prior formation of an 'α,β- unsaturated carbonyl compound-organoborane' complex. (C) 2000 Elsevier Science Ltd.

AB - A study of the reaction of α,β-unsaturated carbonyl compounds with triethylborane under free radical conditions (Brown's reaction) including spectroscopic analyses (11B NMR, IR, EPR) of products and intermediates indicated that these reactions involve the prior formation of an 'α,β- unsaturated carbonyl compound-organoborane' complex. (C) 2000 Elsevier Science Ltd.

KW - Boron and compounds

KW - Carbonyl compounds

KW - Complexation

KW - Enones

KW - Radicals and radical reactions

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U2 - 10.1016/S0040-4039(99)02279-0

DO - 10.1016/S0040-4039(99)02279-0

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

New insight into the mechanism of the reaction between α,β-unsaturated carbonyl compounds and triethylborane (Brown's reaction)

Abstract

Keywords

ASJC Scopus subject areas

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