Deamination of primary amines with dinitrogen tetraoxide at low temperatures: formation of nitrates

Abstract

Treatment of a primary or secondary alkyl primary amine at –78 °C with dinitrogen tetraoxide in the presence of excess of an amidine base gives an improved yield of nitrate ester or of nitrate ester plus alcohol. Use of these conditions significantly reduces the formation of olefins. Reactions of 3α- and 3β-aminocholestane proceed mainly with retention of configuration.