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

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

4 Citations (Scopus)

Résumé

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.

langue originale	Anglais
Pages (de - à)	3678-3686
Nombre de pages	9
journal	Tetrahedron
Volume	72
Numéro de publication	26
Les DOIs	https://doi.org/10.1016/j.tet.2016.03.032
état	Publié - 30 juin 2016
Modification externe	Oui

Accès au document

10.1016/j.tet.2016.03.032

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Contient cette citation

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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.",

year = "2016",

month = jun,

day = "30",

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

language = "English",

volume = "72",

pages = "3678--3686",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "26",

}

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.
Dans: Tetrahedron, Vol 72, Numéro 26, 30.06.2016, p. 3678-3686.

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

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

AN - SCOPUS:84961223899

SN - 0040-4020

VL - 72

SP - 3678

EP - 3686

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -