Tetrahedron

A hydride transfer reaction from salts of carbanions to activated olefins

BA Feit, S Shapira, A Herbst

Index: Feit, Ben-Ami; Shapira, Sarit; Herbst, Amatzya Tetrahedron, 1995 , vol. 51, # 1 p. 317 - 328

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Citation Number: 4

Abstract

A novel reaction-a β-elimination of a hydride ion from carbanion salts RM (R= Li, MgBr) and R2N− Li+, and its transfer to tetra-substituted activated olefins of the type Ar2C= C (CN) CO2R (R= Me, Et), was studied. Yields of the reduced H−-acceptor were used to follow the extent of the H−-transfer reaction. A competing Michael addition reaction of RM to the activated olefin also took place. The effects of the solvation properties of the solvent, the ...