75848-93-0Relevant academic research and scientific papers
Preparation and Dienophilic Reactions of Nitrosyl Cyanide
Horsewood, Peter,Kirby, Gordon W.
, p. 1587 - 1591 (2007/10/02)
Nitrosyl chloride and silver cyanide react at low temperatures to give nitrosyl cyanide (ONCN) which undergoes 1,4-cycloaddition reactions with conjugated dienes to form the corresponding 2-cyano-3,6-dihydro-2H-1,2-oxazines.Thus, the alkaloid, thebaine (1), reacted with a limited quantity of nitrosyl cyanide to form a single adduct (2; R=H, X=CN) convertible into 14-cyanamidocodeinone (3); with an excess of nitrosyl cyanide the related N-cyanomethyl derivative (2; R=X=CN) was formed.Similarly, N-cyano-oxazines have been prepared from buta-1,3-diene and its 2,3-dimethyl, 1-methoxycarbonyl-4-methyl, 1-cyano-4-methyl, and 1,4-bisethoxycarbonyl derivatives.Base-induced rearrangements reactions leading to a pyridone (7), a pyrrolinone (11), and a mixture of dihydrofurans (14) are described.
