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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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