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Synfacts 2006(9): 0902-0902  
DOI: 10.1055/s-2006-942041
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Poly(sulfamide) from Sulfur Dioxide

Contributor(s): Timothy M. Swager, Julian M. W. Chan
A. V. Leontiev, H. V. Rasika Dias, D. M. Rudkevich*
The University of Texas at Arlington, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

An aromatic poly(sulfamide) was synthesized in a single step from p-phenylenediamine and sulfur dioxide, using a mixture of iodine and tertiary amine base as the reagent, and aceto­nitrile as the solvent. Mechanistically, the reaction is believed to involve activation of sulfur dioxide via formation of charge-transfer complexes with the amine bases. While the reaction currently affords the polymer in modest yield and low DP, optimization studies are underway, as well as work involving the use of other phenylenediamine monomers.