
%0 Journal Article
%A Biffin, MEC 
%A Bocksteiner, G 
%A Miller, J 
%A Paul, DB 
%T Reduction by sulphoxides : The mechanism of deoxygenation of heterocyclic N-oxides and tertiary amine N-oxide
%J Australian Journal of Chemistry
%D 1974/04/01
%V 27
%N 4
%P 789-799
%K 
%R https://doi.org/10.1071/CH9740789
%U https://www.publish.csiro.au/paper/CH9740789 
%X 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. 
