Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement

Medhi Boumediene 1 Raphaël Guignard 1 Samir Zard 1
1 DCSO - Laboratoire de synthèse organique
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.
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Submitted on : Monday, January 23, 2017 - 10:38:54 PM
Last modification on : Thursday, February 7, 2019 - 5:03:37 PM

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Medhi Boumediene, Raphaël Guignard, Samir Zard. Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement . Tetrahedron, Elsevier, 2016, 72 (26), pp.3678-3686 ⟨10.1016/j.tet.2016.03.032 ⟩. ⟨hal-01444340⟩

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