Accession Number : AD0692334

Title :   CONCERNING THE MECHANISM OF REDUCTION BY DIMETHYL SULPHOXIDE DEOXYGENATION OF PYRIDINE N-OXIDE,

Corporate Author : DEFENCE STANDARDS LABS MARIBYRNONG (AUSTRALIA)

Personal Author(s) : Biffin,M. E. C. ; Miller,J. ; Paul,D. B.

Report Date : 10 FEB 1969

Pagination or Media Count : 5

Abstract : Previous research has lead to the consideration of the reaction of DMSO with mild oxidants, e.g. heterocyclic N-oxides. Accordingly pyridine N-oxide was heated at 195C for 20 hr with DMSO containing c. H2SO4. Dilution with water followed by removal of the organic decomposition products of DMSO with ether gave a solution of pyridinium salt from which pyridine was isolated as its picrate. The yield was almost quantitative (94%) and these conditions were found to be optimal. G.l.c. analysis indicated that 2% of dimethyl sulphone was present in the reaction mixture. On cooling the mixture after reaction in the absence of acid, crystals, m.p. 185C, were isolated and identified as the methanesulphonic acid salt of pyridine by spectroscopic comparison with an authentic sample. Almost equimolar amounts of pyridine and methanesulphonic acid were formed in the reaction. (Author)

Descriptors :   (*SULFOXIDES, *OXIDATION REDUCTION REACTIONS), (*PYRIDINES, *REDUCTION(CHEMISTRY)), OXIDES, AUSTRALIA

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE