Molecules p. 212 - 218 (2006)
Update date:2022-08-05
Topics:
Diaz, David Diaz
Converso, Antonella
Sharpless, K. Barry
Finn
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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