Letter

DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K.
Org. Lett., 2011, 13 (18), pp 4876–4878
DOI: 10.1021/ol201957n
Publication Date (Web): August 25, 2011
Copyright © 2011 American Chemical Society

Abstract

Abstract Image

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.

Supporting Information


Experimental procedures and full characterization for all compounds (including X-ray data). This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 6,104 Times
Received 20 July 2011
Published online 25 August 2011
Published in print 16 September 2011
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