78002-59-2Relevant articles and documents
Ouverture de dichlorocyclopropanes en presence d'un nucleophile interne. Absence de participation intramoleculaire. Rearrangement concerte en chlorures allyliques
Chiche, Laurent,Christol, Henri,Coste, Jacques,Pietrasanta, Francine,Plenat, Francoise
, p. 164 - 174 (2007/10/02)
It is shown that a conveniently placed internal nucleophile (carboxyl group) is not involved with the rearrangement of a diclorocyclopropane into an allylic chloride.This result appears to support a concerted mechanism of a ?s2 + ?a2 type for this rearrangement.In the products obtained, the allylic chloride may undergo displacement either by solvent (H2O), leading to alcohols, or by the internal carboxyl group, leading to a lactone.