title: 2-Alkylidenesulfol-3-enes by (regio- and) stereoselective cheletropic addition of SO2 to (di)vinylallenes.
abstract: [reaction: see text] The cheletropic addition of SO(2) to divinylallenes is regioselective, taking place at the most substituted vinylallene and at the E unit if vinyl groups of opposite geometry are competing. Diastereofacial differentiation results from the approach of the reagent from the less-substituted direction of the allene and from the concomitant disrotatory movement of the termini of the vinylallene to afford the sterically more congested 2-alkylidenesulfol-3-ene isomer. DFT computations confirm the regio- and the stereoselectivity of these cheletropic additions.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidade de Vigo, 36310 Vigo, Spain.
authors.forename: José A
authors.initials: JA
authors.lastname: Souto
authors.forename: Carlos Silva
authors.initials: CS
authors.lastname: López
authors.forename: Olalla Nieto
authors.initials: ON
authors.lastname: Faza
authors.forename: Rosana
authors.initials: R
authors.lastname: Alvarez
authors.forename: Angel R
authors.initials: AR
authors.lastname: de Lera