2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: multigram display of azide and cyanide components on a versatile scaffold.
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.
Díaz
David Díaz
DD
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, California 92037, USA.
Converso
Antonella
A
Sharpless
K Barry
KB
Finn
M G
MG
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
C431223:2,6-Dichloro-9-thiabicyclo(3.3.1)nonane; D000473:Alkanes; D001386:Azides; D001643:Bridged Bicyclo Compounds; D003486:Cyanides; D013455:Sulfur