Nitrosation of thebaine leading to 7-substituted neopinone derivatives

Abstract

Nitrosation of thebaine hydrochloride with nitrosyl chloride or pentyl nitrite in methanol or ethanol has been shown to give 7-hydroxyiminoneopinone dimethyl or diethyl acetal. Other, bimolecular, products, best prepared by use of nitrosylsulphuric acid as nitrosating agent, arise via Diels–Alder addition of a transient 7-nitrosoneopinone derivative to a second molecule of thebaine.