A REARRANGEMENT IN THE NITRATION OF 3-BETA,17-BETA-DIACETOXY-7-NORANDROST-5-ENE

Authors
HANSON JR HITCHCOCK PB MANICKAVASAGAR R
Citation
Jr. Hanson et al., A REARRANGEMENT IN THE NITRATION OF 3-BETA,17-BETA-DIACETOXY-7-NORANDROST-5-ENE, Journal of the Chemical Society. Perkin transactions. I, (15), 1994, pp. 2073-2076
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
15
Year of publication
1994
Pages
2073 - 2076
Database
ISI
SICI code
0300-922X(1994):15<2073:ARITNO>2.0.ZU;2-7
Abstract
The nitration of 3 beta,17 beta-diacetoxy-7-norandrost-5-ene by fuming nitric acid leads to 3 beta,17 beta-diacetoxy-5 beta-nitroxy-6 alpha- nitro-7-norandrostane and to the rearrangement product 2. A number of minor products were also identified. The formation of these can be rat ionalized in terms of a Markownikoff directed diaxial (5 beta,6 alpha) addition to the Delta(5)-double bond of the B-norsteroid which contra sts with the 5 alpha,6 beta-diaxial addition found in the normal stero ids.