Tetrahedron

Reactions of oxiranes with alkali metals: intermediacy of radical-anions

KN Gurudutt, MA Pasha, B Ravindranath, P Srinivas

Index: Gurudutt, K. N.; Pasha, M. A.; Ravindranath, B.; Srinivas, P. Tetrahedron, 1984 , vol. 40, # 9 p. 1629 - 1632

Full Text: HTML

Citation Number: 15

Abstract

Reaction of oxiranes with alkali metals in aprotic solvents yields a variety of products depending on the nature of the metal and the structure of the oxirane. Deoxygenation to olefins is the major reaction in case of lithium. Rearrangement to carbonyl compounds, reduction to alcohols and formation of dimeric products occur when oxiranes are treated with sodium. All the reactions could be rationalised by a mechanism involving an initial single ...