TY - JOUR
T1 - Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane
AU - Block, Eric
AU - Glass, Richard S.
AU - DeOrazio, Russell
AU - Lichtenberger, Dennis L.
AU - Pollard, John R.
AU - Russell, Erin E.
AU - Schroeder, T. Benjamin
AU - Thiruvazhi, Mohan
AU - Toscano, Paul J.
PY - 1997/5
Y1 - 1997/5
N2 - 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 bis-sulfides (±)-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. Bis-sulfides 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.
AB - 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 bis-sulfides (±)-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. Bis-sulfides 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.
UR - https://www.scopus.com/pages/publications/0002986646
UR - https://www.scopus.com/pages/publications/0002986646#tab=citedBy
U2 - 10.1055/s-1997-6136
DO - 10.1055/s-1997-6136
M3 - Article
AN - SCOPUS:0002986646
SN - 0936-5214
SP - 525
EP - 528
JO - Synlett
JF - Synlett
IS - SPEC. ISS.
ER -