Collect. Czech. Chem. Commun. 1984, 49, 2410-2414

Evolution thermique de N-oxydes D'ω-dialkylamino alcanols-1

Didier Barbry and Bruno Hasiak

Laboratoire de Synthèse Organique - C4 Université des Sciences et Techniques de Lille 596 55 Villeneuve d'Ascq Cédex, France


The thermolysis of ω-dimethylamino-1-alkanol N-oxides affords ω-hydroxy-1-alkenes with dimethylhydroxylamine in good yields. The other basic products ( amino alcohol and isoxazolidine) involve oxidation-reduction process between the tertiary amine N-oxide and dimethylhydroxylamine, followed by 1,3-dipolar cycloaddition reaction. Pyrolysis of 5-piperidino-1-pentanol N-oxide proceeds on a path similar to the N-dimethyl compounds. The elimination of an hydrogen atom of the heterocycle does not occur: the preferred planar transition state cannot be attained because of the steric requirements of the ring.