Synthesis of sulfenyl dipyrroles via reaction of α-free pyrroles with thionyl chloride

Author:

Beh Michael H.R.1,Smith Craig D.1,Robertson Katherine N.2,Thompson Alison1

Affiliation:

1. Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS, B3H 4R2, Canada.

2. Department of Chemistry, Saint Mary's University, Halifax, NS, B3H 3C3, Canada.

Abstract

Sulfenyl dipyrroles feature two pyrroles linked via a sulfenyl bridge. The synthesis of sulfenyl dipyrroles has typically involved SCl2 as the sulfur source. However, SCl2 is no longer readily available within North America and Europe. Herein we report a new synthesis of sulfenyl dipyrroles using SOCl2 as the sulfur source and reductant. Although five new sulfenyl dipyrroles were synthesized and isolated via this route, functional group tolerance proved limited. A potential mechanism for the reaction, involving reduction of a sulfinyl moiety by SOCl2, is briefly explored.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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