4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Abstract

Heterocyclic azo compounds, prepared from corresponding amines in one step, are used as effective oxidants for the conversion of thiols into symmetrical disulfides in high yields. Among the studied azo compounds, 4,4′-azopyridine was found to be very efficient for the odorless conversion of alkyl halides into disulfides in the presence of thiourea. An attractive feature of this azo compound is that its obtained solid side product hydrazine is easily separated by filtration and can be recycled to its azo compound for further use.

GRAPHICAL ABSTRACT

Keywords:

• azopyridine
• azo compounds
• disulfide
• thiol
• alkyl halide

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

Financial support of this work from the Research Council of Shiraz University is gratefully acknowledged.