Laboratoire d'Etudes Dynamiques et Structurales de la Sélectivité, Université Scientifique et Médicale de Grenoble, B. P. 53X, 38041 Grenoble Cédex, France
Institut de Chimie, Université de Léningrad 199164, U.S.S.R.
Abstract:
Reduction of 2 cyclopropenyl esters and alcohols with lithium aluminium hydride is selective; at low temperatures (0°) the double bond is not reduced, but at higher temperatures (65°) the reduction is complete and only the cyclopropylmethanol is obtained. The reduction of the double bond is regioselective (the most stable carbanion is formed) and stereospecific (the hydride attack on the double bond occurs cis to the functional group). This stereospecificity can be explained through the initial formation of an alkoxylaluminium hydride followed by an intramolecular reduction of the double bond. Similar results have been obtained in the reduction of functionalised methylenecyclopropanes.