
TY  - JOUR
A1  - Biffin, MEC 
A1  - Bocksteiner, G 
A1  - Miller, J 
A1  - Paul, DB 
T1  - Reduction by sulphoxides : The mechanism of deoxygenation of heterocyclic N-oxides and tertiary amine N-oxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1974
VL  - 27
IS  - 4
SP  - 789
EP  - 799
KW  - 
UR  - https://doi.org/10.1071/CH9740789 
N2  - 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. 
ER  -

