Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane

Eric Block, Richard S Glass, Russell DeOrazio, Dennis L Lichtenberger, John R. Pollard, Erin E. Russell, T. Benjamin Schroeder, Mohan Thiruvazhi, Paul J. Toscano

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)525-528
Number of pages4
JournalSynlett
Issue numberSPEC. ISS.
StatePublished - May 1997

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Hexanes
Sulfur
Sulfides
Oxides
Oxidation
Ionization potential
Photoelectron spectroscopy
Cyclic voltammetry
Wavelength

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Block, E., Glass, R. S., DeOrazio, R., Lichtenberger, D. L., Pollard, J. R., Russell, E. E., ... Toscano, P. J. (1997). Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane. Synlett, (SPEC. ISS.), 525-528.

Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane. / Block, Eric; Glass, Richard S; DeOrazio, Russell; Lichtenberger, Dennis L; Pollard, John R.; Russell, Erin E.; Schroeder, T. Benjamin; Thiruvazhi, Mohan; Toscano, Paul J.

In: Synlett, No. SPEC. ISS., 05.1997, p. 525-528.

Research output: Contribution to journalArticle

Block, E, Glass, RS, DeOrazio, R, Lichtenberger, DL, Pollard, JR, Russell, EE, Schroeder, TB, Thiruvazhi, M & Toscano, PJ 1997, 'Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane', Synlett, no. SPEC. ISS., pp. 525-528.
Block, Eric ; Glass, Richard S ; DeOrazio, Russell ; Lichtenberger, Dennis L ; Pollard, John R. ; Russell, Erin E. ; Schroeder, T. Benjamin ; Thiruvazhi, Mohan ; Toscano, Paul J. / Significant intramolecular sulfur-sulfur interactions in cis- and trans-2,3-dimethyl-5,6-dithiabicyclo-[2.1.1]hexane. In: Synlett. 1997 ; No. SPEC. ISS. pp. 525-528.
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abstract = "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.",
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