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Allenmark, Stig, Grainger, Richard S., Olsson, Susanne and Patel, Bhaven (2011) Resolution and determination of the absolute configuration of the enantiomers of a trans-α-disulfoxide. European Journal of Organic Chemistry, 2011 (22). pp. 4089-4092. ISSN 1434-193X
The trans isomer of 2,7-di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxide, a vic-disulfoxide of the highest thermal stability reported to date, has been resolved into its enantiomers by preparative chiral liquid chromatography. This represents the first resolution achieved of a vic-disulfoxide. The absolute configuration of the isolated enantiomers has been determined to be (+)-(S,S), (–)-(R,R) from a comparison of experimental and calculated ECD and VCD spectra. The long-wavelength ECD band at about 330 nm had a positive sign in the (+)-(S,S)-form and a negative sign in the (–)-(R,R)-enantiomer. A photocatalyzed slow decrease in optical activity was observed in solution, most likely due to racemization by homolytic (O)S–S(O) bond cleavage and bissulfinyl radical recombination.
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