EVOLUTION THERMIQUE DE N-OXYDES D'ω-DIALKYLAMINO ALCANOLS-1
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 thesteric requirements of the ring.
Barbry, Didier,Hasiak, Bruno
p. 2410 - 2414
(2007/10/02)
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