Nitroamine radicals as intermediates in the functionalization of non-activated carbon atoms

Abstract

Photolysis of N-iodonitroamines generated in situ from the steroidal nitroamines 6β-nitroamino-5α-cholestan-3β-ol acetate, 6β-nitroamino-5α-cholestane-3β,5α-diol diacetate, and 20R-nitroaminopregn-5-en-3-ol acetate removes hydrogen atoms from the Me-18 and Me-19 groups to give 6β-,19-N-nitroepinino-5α-cholestan-3β-ol acetate, 6β,19-N-nitroepinino-5α-cholestane-3β5α-diol diacetate, and 18,20R-N-nitroepiminopregn-5-en-3β-ol acetate.