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Resolution and Determination of the Absolute Configuration of the Enantiomers of a trans-α-Disulfoxide

✍ Scribed by Stig Allenmark; Richard S. Grainger; Susanne Olsson; Bhaven Patel

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
395 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

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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