114552-53-3Relevant academic research and scientific papers
Preparation of Stable, Camphor-Derived, Optically Active Allyl and Alkyl Sulfoxides and Thermal Epimerization of the Allyl Sulfoxides
Goodridge, Richard J.,Hambley, Trevor W.,Haynes, Richard K.,Ridley, Damon D.
, p. 2881 - 2889 (2007/10/02)
(+)-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.
