Accession Number:

AD0784726

Title:

Reduction by Sulphoxides: The Mechanism of Deoxygenation of Heterocyclic N-Oxides and Tertiary Amine N-Oxides,

Descriptive Note:

Corporate Author:

DEFENCE STANDARDS LABS MARIBYRNONG (AUSTRALIA)

Report Date:

1973-11-20

Pagination or Media Count:

11.0

Abstract:

Heterocyclic and tertiary amine N-oxides undergo an acid-catalysed deoxygenation by sulphoxides at elevated temperatures. The reductions are rationalized by postulating the formation of an initial coordination complex formed by attack of the nucleophilic N-oxide oxygen atom on the sulphur atom of the sulphoxide or its conjugate base. This complex may undergo an internal redox reaction to give a sulphone and amine or alternatively be attacked by a nucleophilic species presumably sulphoxide oxygen to produce a sulphinate and amine. Both decomposition pathways were observed. Deoxygenation of heterocyclic N-oxides, however, proceeds primarily by the second route and that of aliphatic amine oxides by the first decomposition process. These observations are rationalized mechanistically. The effect of varying the N-oxide substrates and the sulphoxides has also been examined. Author

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE