Intramolecular catalysis. Part III. Effect of a neighbouring hydroxy-group on the opening of steroidal aziridines with azide anions
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1037-1042
- https://doi.org/10.1039/p19760001037
Abstract
5α,6α-Iminocholestan-3β-ol (IV) and its 3α-hydroxy-isomer (V) have been prepared and their structures established. Their reactions with sodium azide in acetone–water (2 : 1) produce the corresponding trans-diaxial amino-azides. The ratio of the reaction rates is ca. 1 : 2, respectively. The mechanisms of the reactions of the steroidal aziridines are discussed and comparison is made between these compounds and the related epoxides.Keywords
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