ORGANIC CHEMICAL REAGENTS.³ III. β-PHENYLHYDROXYLAMINE AND CUPFERRON.

Chemistry of the Nitric Oxide-Releasing Diazeniumdiolate (“Nitrosohydroxylamine”) Functional Group and Its Oxygen-Substituted Derivatives

“…The most common precursors to the C -diazeniumdiolates are the organohydroxylamines. Since some of the C -diazeniumdiolates are acid sensitive, the best general preparative methods have been neutral or basic reactions as illustrated by an early preparation of Cupferron ( 5 ) via nitrosation of phenylhydroxylamine with amyl nitrite/ammonia or methyl nitrite/ammonia (eq 1). Recent applications of this method have resulted in the preparation of a variety of Cupferron derivatives as well as 11 aliphatic C -diazeniumdiolates as the ammonium salts .…”

Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: solvent-free microwave-assisted stereoselective synthesis and theoretical calculations

“…Methylation of nitrogen does not reduce the reactivity (entries 4-7). Phenylhydroxylamine 1c was used in further excess (ratio ketone/ phenylhydroxylamine 1 : 3) because of its known degradability at temperature higher than 50 C. 34 Attempts to reduce byproducts by lowering power of MW (200 or 400 W) or by reducing the maxim temperature were unnecessary. In all cases the E-isomer was the only obtained with the exceptions of compounds 4d and 4h for which small quantities of Z isomers (ratio E/Z: 78 : 22 and 75 : 25 for 4d and 4h, respectively) were obtained.…”

N-Nitroso Compounds

“…The nitrosation itself is carried out with either pentyl nitrite [66] or butyl nitrite [67]. The reaction is carried out in ether in the presence of large excess of gaseous ammonia at 0°C.…”