Hydrocyanation. Part X. Cleavage of epoxides with hydrogen cyanide and triethylaluminium and with diethylaluminium cyanide
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 17,p. 2365-2377
- https://doi.org/10.1039/j39700002365
Abstract
Steroidal epoxides are smoothly cleaved by hydrogen cyanide–triethylaluminium and by diethylaluminium cyanide under mild conditions to give the corresponding trans-diaxial β-cyanohydrins, except for the 5β, 10β-epoxide (XXVIb) which gives the cis-β-cyanohydrin (XXVIII) as well as the major, trans-diaxial product (XXVIIb). The compounds examined included the 5α,6α-, 5β,6β-, 9α,11α-, 9β,11β-, 16α,17α-, 2α,3α-, 3α,4α-, 11α,12α-, 5α,10α-, and 5β,10β-epoxides. The successful cleavage of the 9α,11α-epoxides (VIII) to give the 9α-hydroxy-11β-cyano-steroid (IX) is significant in view of the fact that 9α,11α-epoxides are known to resist cleavage by lithium aluminium hydride or hydrogen halides. β-Cyanohydrins are also obtained from the corresponding β-bromohydrins by treatment with hydrogen cyanide and triethylaluminium.Keywords
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