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

doi:10.3390/11040212

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

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

David D. Díaz ² , Antonella Converso ¹ , K. B. Sharpless ¹ and M. G. Finn 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.

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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.

AMA 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(4):212-218.

Chicago/Turabian Style

Díaz, David D.; Converso, Antonella; Sharpless, K. B.; Finn, M. G. 2006. "2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold." Molecules 11, no. 4: 212-218.

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