2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: a privileged, bivalent scaffold for the display of nucleophilic components.
The title compound, the condensation product of sulfur dichloride and 1,5-cyclooctadiene, is a reliable acceptor of a wide variety of heteroatom nucleophiles, sometimes in reversible fashion. Optical resolution of the core structure has been achieved and preserved in succeeding transformations. The high reactivity and reliable stereochemical control afforded by this system illustrates the power of neighboring-group participation by the sulfur center.
Converso
A
A
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037.
Burow
K
K
Marzinzik
A
A
Sharpless
K B
KB
Finn
M G
MG
D000473:Alkanes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
C431223:2,6-Dichloro-9-thiabicyclo(3.3.1)nonane; D000473:Alkanes; D001643:Bridged Bicyclo Compounds