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

Medhi Boumediene (1) , Raphaël F. Guignard (1) , Samir Zard (1)

1 DCSO - Laboratoire de synthèse organique

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.

Domaines: Chimie organique

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