Organic Letters 2011-09-16

DABCO-bis(sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: utility in sulfonamide and sulfamide preparation.

Holly Woolven, Carlos González-Rodríguez, Isabel Marco, Amber L Thompson, Michael C Willis

Index: Org. Lett. 13 , 4876-4878, (2011)

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Abstract

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.© 2011 American Chemical Society