Reaction of Nitrosyl Chloride with Steroid 5-Enes. Nuclear Magnetic Resonance as a Stereochemical Tool in Steroids

Alfred Hassner, Clayton Heathcock

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125 Scopus citations

Abstract

Steroid 5-enes, on treatment with an excess of nitrosyl chloride, give 5α-chloro-6β-nitro steroids in good yield. These nitrochloro adducts are transformed by pyridine into the corresponding 6-nitro-5-enes. The latter are reduced stereospecifically by sodium borohydride to 6α-nitro 5α-steroids. 6β-Nitro-5α-chlorocholestan-3β-ol acetate reacts with chromous chloride in methanolic hydrochloric acid to give 6-oximino-5α-methoxycholestan-3β-ol acetate. It is shown that the half-width of a band in the n.m.r. may be correlated with the conformation of the proton giving rise to the band. Thus, equatorial protons give rise to a narrow band (5-12 c.p.s.), while axial protons give a broad band (15-30 c.p.s.).

Original languageEnglish
Pages (from-to)1350-1355
Number of pages6
JournalJournal of Organic Chemistry
Volume29
Issue number6
DOIs
StatePublished - 1 Jun 1964
Externally publishedYes

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