2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: multigram display of azide and cyanide components on a versatile scaffold

David Díaz Díaz; Antonella Converso; K Barry Sharpless; M G Finn

doi:10.3390/11040212

2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: multigram display of azide and cyanide components on a versatile scaffold

Molecules. 2006 Mar 27;11(4):212-8. doi: 10.3390/11040212.

Authors

David Díaz Díaz¹, Antonella Converso, K Barry Sharpless, M G Finn

Affiliation

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.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes / chemistry*
Azides / chemistry*
Bridged Bicyclo Compounds / chemistry*
Cyanides / chemistry*
Magnetic Resonance Spectroscopy
Sulfur / chemistry

Substances

2,6-Dichloro-9-thiabicyclo(3.3.1)nonane
Alkanes
Azides
Bridged Bicyclo Compounds
Cyanides
Sulfur