N-Phenylhydroxylamine → HCID 15656242, compound

Participants

Reaction Steps

A stirred mixture containing dioxane (12 mL), 3 mL of 1-octene, 1 g of 4A Molecular Sieves, and 0.051 g (0.11 mmol) of (2,6-dipicolinato)MoO2 (hexamethyl phosphoramide) is heated at reflux (ca. 100° C.) under a nitrogen atomosphere while a toluene solution (50 mL) of N-phenyl hydroxylamine (1.26 g, 11.6 mmol) is added dropwise over a 24 hr period. After heating an additional 6-12 hr, the mixture was allowed to cool and the volatiles were removed by evaporation at reduced pressure and the residue chromatographed over silica gel. Elution with pentane afforded phenyl trans-2-octenyl amine (>95% one isomer by NMR, GC/MS) in 20-30% yield based on the hydroxylamine. Later fractions contained aniline, azobenzene and azoxybenzene.

Provenance & Evidence