N-Phenylhydroxylamine → N-(Cyclohex-3-en-1-yl)aniline

Participants

Reaction Steps

A stirred mixture containing dioxane (12 mL), 3 mL of cyclohexene, 1g of 4A Molecular Sieves, and 0.11 mmol of (2,6-dipicolinato)(HMPA)Mo(O) (ONPh) is heated at reflux (ca. 100° C.) under a nitrogen atmosphere 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 12-24 hr, the mixture was allowed to cool and the volatiles were removed by evaporation at reduced pressure. Chromatography of the residue over silica gel and elution with pentane afforded phenyl 3-cyclohexenyl amine (>95% one isomer by NMR, GC/MS) in 15-25% yield based on the hydroxylamine. Later fractions contained aniline, azobenzene and azoxybenzene.

Provenance & Evidence