13C nuclear magnetic resonance studies of the products of reaction of acetaldehyde and of simple ketones in liquid ammonia, in hydrazine hydrate, and in some substituted hydrazine solutions

Abstract

¹³ C N.m.r. shows that acetaldehyde rapidly forms the classical ‘aldehyde–ammonia’ in liquid ammonia, together with 2,4,6-trimethylhexahydro-1,3,5-triazine. For the first time, the formation of gem-aminohydroxy products corresponding to aldehyde–ammonia adducts by a range of ketones under the same conditions has been observed directly. In parallel studies, the products formed by acetaldehyde and by various ketones in hydrazine hydrate and in some simply substituted hydrazines have also been determined. It has been possible not only to detect hydrazones, azines, and a hexahydrotetrazine with the appropriate reagents, but also to identify the formation of gem-hydrazino-hydroxy adducts corresponding to aldehyde–ammonia adducts.