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Steroids. V. Conjugated steroid nitriles via phosphonates (1,2)

Authors :
R. M. Ramer
Ajay K. Bose
Source :
Steroids. 11:27-35
Publication Year :
1968
Publisher :
Elsevier BV, 1968.

Abstract

Steroid ketones were found to react with diethyl cyanomethylphosphonate in the presence of dimsyl anion and dimethyl sulfoxide at room temperature forming conjugated nitriles. Ketones at positions 2,4,6,7,12, and 15 readily afforded unsaturated nitriles. The yield of Δ 4 -3-cyano-methylene steroids from Δ 4 -3-ketosteroids was high under these conditions. The sterically hindered ketone from lanosterol also could be converted to an unsaturated nitrile. Ketones at positions 1 and 11 were found to be unreactive even when dimsyl anion and dimethyl sulfoxide were used. 16-Ketoprogesterone did not react, probably because it is a β -diketone.

Details

ISSN :
0039128X
Volume :
11
Database :
OpenAIRE
Journal :
Steroids
Accession number :
edsair.doi.dedup.....e039170b6ffbfbf8aa4fb6c79dd26922
Full Text :
https://doi.org/10.1016/s0039-128x(68)80049-2