A Method for the Contra-thermodynamic Isomerization of Cyclic Trisubstituted Alkenes

Raphaël F. Guignard (1) , Laurent Petit (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

A simple sequence for the net contra-thermodynamic isomerization of cyclic trisubstituted alkenes is reported consisting of a radical addition of p-chlorothiophenol, followed by oxidation to the sulfoxide and thermal syn-elimination to give the least substituted isomeric cycloalkene.

Raphaël F. Guignard, Laurent Petit, Samir Z. Zard. A Method for the Contra-thermodynamic Isomerization of Cyclic Trisubstituted Alkenes. Organic Letters, 2013, 15 (16), pp.4178-4181. ⟨10.1021/ol4018744⟩. ⟨hal-00966611⟩