114552-53-3

Upstream product

• 114552-49-7 (+)-(1R,2S,3R,4S)-1,7,7-Trimethyl-3-(benzylthio)bicyclo<2.2.1>heptan-2-ol 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 114552-41-9 (1R)-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 

Relevant academic research and scientific papers

Preparation of Stable, Camphor-Derived, Optically Active Allyl and Alkyl Sulfoxides and Thermal Epimerization of the Allyl Sulfoxides

(+)-Camphor is converted by thioalkylation of the lithium enolate with allyl and alkyl p-toluenethiosulfonates into exo-3-(allylthio)- and exo-3-(alkylthio)camphors, which upon reduction with diisobutylaluminum hydride give the coresponding exo-(allylthio)- and exo-(alkylthio)isoborneols.Oxidation of the sulfides with m-chloroperbenzoic acid gives the exo-(allylsulfinyl)- and exo-(alkylsulfinyl)isoborneols in a stereochemically pure state.The configuration at sulfur in the sulfoxides is determined by X-ray crystalography of the allyl derivative to be SS; this configuration implies that the exo-hydroxyl group at C2 controls the stereochemical outcome of the oxidation.The allylic sulfoxides are stable at room temperature, but upon heating through their melting points undergo a remarkable and generally quantitative rearrangement into the RS epimers.