α-Sulfinylcarbanions (1) derived from methyl-substituted sulfoxides readily react with arenesulfinic esters (2) to give the corresponding β-disulfoxides (3) in good yields. The reaction was conducted using (−)-menthyl (−)-(S)-benzenesulfinate ((−)-(S)-2b), (−)-menthyl (−)-(S)-p-toluenesulfinate ((−)-(S)-2c), and α-p-tolylsulfinylcarbanion derived from (+)-(R)- or (−)-(S)-methyl p-tolyl sulfoxide to produce (R,S)- and/or (S,S)-diastereoisomers of five β-disulfoxides (3a–e). The configurational assignment for the diastereoisomers obtained was accomplished by a combination of NMR and polarimetric analyses.
Die Reaktion von entsprechenden Lithioarylmethylsulfoxiden (I) (aus dem entsprechenden Methylsulfoxid mit Li‐diethylamid) mit optisch aktiven Estern wie (II) verläuft enantioselektiv unter Bildung vontoptisch aktiven β‐Keto‐sulfoxiden wie (III) und entsprechenden Arylmethylsulfoxiden (IV) mit umgekehrter Konfiguration.
The basicities of nine meta- and para-substituted diphenyl sulfoxides have been determined spectrophotometrically in sulfuric acid media. The pKBH+ values thus obtained indicate that these sulfoxides possess rather weak basicities (pKBH+; −3.67–−5.74). and these pKBH+ values gave a good correlation with Brown-Okamoto’s σ+ values, (ρ=−2.00), instead of σ-values. These observations seem to suggest a considerable conjugative interaction between phenyl groups and sulfoxide group of these diphenyl sulfoxides.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.