Nitrosyl chloride adduct of methyl oleate

Nitrosyl chloride was added to methyl oleate on a preparative scale to give the adduct in essentially quantitative yield. The chlorine of the adduct was quite labile; was replaced by methoxyl, hydroxyl, acetoxyl, piperidino, and amino groups; and was eliminated to give the unsaturated nitroso compound. Under any conditions only 15–20% of the nitroso group of the adduct isomerized to oximino. Reduction with zinc and acetic acid gave the hydroxylamino derivative