Ouverture de dichlorocyclopropanes en présence d'un nucléophile interne. Absence de participation intramoléculaire. Réarrangement concerté en chlorures …

…, H Christol, J Coste, F Pietrasanta…

Index: Chiche, Laurent; Christol, Henri; Coste, Jacques; Pietrasanta, Francine; Plenat, Francoise Canadian Journal of Chemistry, 1981 , vol. 59, p. 164 - 174

Full Text: HTML

Citation Number: 4

Abstract

It is shown that a conveniently placed internal nucleophile (carboxyl group) is not involved with the rearrangement of a dichlorocyclopropane into an allylic chloride. This result appears to support a concerted mechanism of a σs2+ σa2 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.[Journal ...