A rearrangement in the nitration of 3β, 17β-diacetoxy-7-norandrost-5-ene

Abstract

The nitration of 3β,17β-diacetoxy-7-norandrost-5-ene by fuming nitric acid leads to 3β,17β-diacetoxy-5β-nitroxy-6α-nitro-7-norandrostane and to the rearrangement product 2. A number of minor products were also identified. The formation of these can be rationalized in terms of a Markownikoff directed diaxial (5β,6α) addition to the Δ⁵-double bond of the B-norsteroid which contrasts with the 5α,6β-diaxial addition found in the normal steroids.