Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement This article is dedicated to Professor Neil Garg, recipient of the 2015 Tetrahedron Young Investigator award

Mehdi Boumediene; Raphaël F. Guignard; Samir Z. Zard

doi:10.1016/j.tet.2016.03.032

Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement This article is dedicated to Professor Neil Garg, recipient of the 2015 Tetrahedron Young Investigator award

Mehdi Boumediene
, Raphaël F. Guignard
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

4 Citations (Scopus)

Abstract

Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.

Original language	English
Pages (from-to)	3678-3686
Number of pages	9
Journal	Tetrahedron
Volume	72
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2016.03.032
Publication status	Published - 30 Jun 2016
Externally published	Yes

Keywords

Aromatics
Radical chain
von Auwers rearrangement

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10.1016/j.tet.2016.03.032

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title = "Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement This article is dedicated to Professor Neil Garg, recipient of the 2015 Tetrahedron Young Investigator award",

abstract = "Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.",

keywords = "Aromatics, Radical chain, von Auwers rearrangement",

author = "Mehdi Boumediene and Guignard, \{Rapha{\"e}l F.\} and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd.",

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doi = "10.1016/j.tet.2016.03.032",

language = "English",

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Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement This article is dedicated to Professor Neil Garg, recipient of the 2015 Tetrahedron Young Investigator award. / Boumediene, Mehdi; Guignard, Raphaël F.; Zard, Samir Z.
In: Tetrahedron, Vol. 72, No. 26, 30.06.2016, p. 3678-3686.

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

TY - JOUR

T1 - Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement This article is dedicated to Professor Neil Garg, recipient of the 2015 Tetrahedron Young Investigator award

AU - Boumediene, Mehdi

AU - Guignard, Raphaël F.

AU - Zard, Samir Z.

PY - 2016/6/30

Y1 - 2016/6/30

N2 - Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.

AB - Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.

KW - Aromatics

KW - Radical chain

KW - von Auwers rearrangement

U2 - 10.1016/j.tet.2016.03.032

DO - 10.1016/j.tet.2016.03.032

M3 - Article

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SN - 0040-4020

VL - 72

SP - 3678

EP - 3686

JO - Tetrahedron

JF - Tetrahedron

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