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Molecules 2006, 11(4), 212-218; doi:10.3390/11040212
Article

2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold

2
,
1
,
1
 and
1,*
1 Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, California 92037, USA 2 Departamento de Química Orgánica, Universidad Autónoma de Madrid, 28049 Madrid, Spain
* Author to whom correspondence should be addressed.
Received: 16 March 2006 / Accepted: 27 March 2006 / Published: 27 March 2006
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Abstract

2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, easily available by an improved condensation of sulfur dichloride, sulfuryl chloride, and 1,5-cyclooctadiene, is a well- behaved scaffold for the nucleophilic substitution of azides and cyanides via neighboring- group participation by the sulfur atom. The products are isolated in high yields with purity >95% by simple extraction and washing protocols.
Keywords: Sulfur mustard; azides; cyanides; neighboring-group participation; multigram synthesis. Sulfur mustard; azides; cyanides; neighboring-group participation; multigram synthesis.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Díaz, D.D.; Converso, A.; Sharpless, K.B.; Finn, M.G. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold. Molecules 2006, 11, 212-218.

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