title: 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: multigram display of azide and cyanide components on a versatile scaffold.
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.
authors.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.
authors.forename: David Díaz
authors.initials: DD
authors.lastname: Díaz
authors.forename: Antonella
authors.initials: A
authors.lastname: Converso
authors.forename: K Barry
authors.initials: KB
authors.lastname: Sharpless
authors.forename: M G
authors.initials: MG
authors.lastname: Finn
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013455:Sulfur / Q000737:chemistry
chemical_list: C431223:2,6-Dichloro-9-thiabicyclo(3.3.1)nonane; D000473:Alkanes; D001386:Azides; D001643:Bridged Bicyclo Compounds; D003486:Cyanides; D013455:Sulfur