2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: multigram display of azide and cyanide components on a versatile scaffold |
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| Authors: | Díaz David Díaz Converso Antonella Sharpless K Barry Finn M G |
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| Affiliation: | Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, California 92037, USA. |
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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. |
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