Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The stereochemistry of alkali metal/ammonia reductions of stilbenes: Application in the synthesis of 14C-labelled meso-hexoestrol

DJ Collins and JJ Hobbs

Australian Journal of Chemistry 36(3) 619 - 625
Published: 1983

Abstract

Some α,α-disubstituted stilbenes were reduced with lithium, sodium or potassium in anhydrous liquid ammonia by two procedures: (A) the alkali metal was added to a solution of the stilbene in ammonia/tetrahydrofuran; and (B) a solution of the stilbene in tetrahydrofuran was added to a preformed blue solution of the alkali metal in ammonia. For the more sterically crowded stilbenes the ratio of bibenzyl diastereoisomers formed differed according to the alkali metal and the reduction procedure used. The results were exploited in a synthesis of 2-14C-labelled meso-hexoestrol.

https://doi.org/10.1071/CH9830619

© CSIRO 1983

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions