Nucleophilic substitution by grignard reagents on sulfur mustards.
With proper activation of the leaving group, sulfur mustards react with Grignard reagents with neighboring group participation of the sulfur atom. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane is especially useful in this regard, providing clean reactivity with organomagnesium nucleophiles on a topologically constrained scaffold.
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Antonella
A
Converso
Pierre-Loïc
PL
Saaidi
K Barry
KB
Sharpless
M G
MG
Finn
D018360:Crystallography, X-Ray; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D009150:Mustard Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
D007202:Indicators and Reagents; D009150:Mustard Compounds; D013455:Sulfur