Reactions of resonance stabilized anions. 34. Synthesis of nitrocyclopropanes by cyclization of. gamma.-chloro-. gamma.-nitro carboxylic esters and derivatives

GA Russell, M Makosza…

Index: Russell,G.A. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 1195 - 1199

Full Text: HTML

Citation Number: 22

Abstract

Michael addition of the anions of 1-chloro-1-nitro alkanes to a, P-unsaturated esters, nitriles, or ketones yields y-chloro-y-nitro esters, nitriles, or ketones, which in the presence of base undergo cyclization to form the P-alkyl-2-nitrocyclopropanecarboxylic ester, cyclopropanenitrile, or cyclopropyl methyl ketone, in which the nitro group and the ester, nitrile, or ketone functions are in a trans arrangement. The reaction appears to proceed via ...

Related Articles:

(R)-(-)-and (S)-(+)-Synadenol: Synthesis, Absolute Configuration, and Enantioselectivity of Antiviral Effect x

[Qui, Yao-Ling; Hempel, Andrew; Camerman, Norman; Camerman, Arthur; Geiser, Fiona; et al. J. Med. Chem., 1998 , vol. 41, # 26 p. 5257 - 5264]

Synthesis and deamination of a deuterium-labeled spiropentylamine

[Applequist,D.E. et al. Journal of the American Chemical Society, 1970 , vol. 92, p. 4614 - 4617]

More Articles...