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Synlett 1997; 1997(SI): 525-528
DOI: 10.1055/s-1997-6136
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Significant Intramolecular Sulfur-Sulfur Interactions in cis- and trans-2,3-Dimethyl-5,6-dithiabicyclo[2.1.1]hexane

Eric Block1 , Richard S. Glass2 , Russell DeOrazio3 , Dennis L. Lichtenberger4 , John R. Pollard4 , Erin E. Russell4 , T. Benjamin Schroeder4 , Mohan Thiruvazhi3 , Paul J. Toscano3
  • 1Department of Chemistry, State University of New York at Albany, Albany, NY 12222, Fax 518 442 3462; e-mail: eb801@csc.albany.edu
  • 2Department of Chemistry, The University of Arizona, Tucson, AZ 85721, Fax 520 621-8407; e-mail: glass@ccit.arizona.edu
  • 3Department of Chemistry, State University of New York at Albany, Albany, NY 12222
  • 4Department of Chemistry, The University of Arizona, Tucson, AZ 85721
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Publication Date:
31 December 2000 (online)

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Reduction of (±)-(1α, 2α, 3β, 4α, 5β)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (3a) and (1α, 2α, 3α, 4α, 5β)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (3b) gives the bissulfides (±)-trans-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane (2a) and cis-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane (2b), respectively. Bissulfides 2a and 2b, on oxidation with one equivalent of m-CPBA, give 3a and 3b, respectively, as the only products. Significant sulfur-sulfur interactions in 2a and 2b are indicated by the long-wavelength UV maxima, the lowered ionization potentials, as measured by photoelectron spectroscopy, and the lowered oxidation potentials, as found by cyclic voltammetry.

5,6-dithiabicyclo[2.1.1]hexanes - sulfur-sulfur interactions - cyclic voltammetry - photoelectron spectroscopy - cation radicals