The Journal of Organic Chemistry

Facile synthesis of allylic nitro compounds by N, N-dimethylethylenediamine-catalyzed condensation of aliphatic and alicyclic ketones with primary nitroalkanes

R Tamura, M Sato, D Oda

Index: Tamura, Rui; Sato, Masahiro; Oda, Daihei Journal of Organic Chemistry, 1986 , vol. 51, # 23 p. 4368 - 4375

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Citation Number: 64

Abstract

Aliphatic as well as alicyclic ketones condense with primary nitroalkanes in the presence of N, N-dimethylethylenediamine (1) to give allylic nitro compounds selectively in good to excellent yields without forming a-nitro olefins. Condensation of 2-alkanones and 2- methylcyclopentanone with nitromethane produces the products of thermodynamic control, while the product of kinetic control is obtained from 2-methylcyclohexanone. ...