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Optically active 1,3,2-benzodithiazole S-oxides : A study of rates of racemization and absolute stereochemistry
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- Allenmark, Stig (author)
- Department of Organic Chemistry, Göteborg University, Göteborg, Sweden
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- Oxelbark, Joakim, 1970- (author)
- Department of Organic Chemistry, Göteborg University, Göteborg, Sweden
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(creator_code:org_t)
- Taylor & Francis, 1996
- 1996
- English.
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In: Enantiomer (Basel. Print). - : Taylor & Francis. - 1024-2430 .- 1607-8446. ; 1:1, s. 13-22
- Related links:
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https://urn.kb.se/re...
Abstract
Subject headings
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- The optical isomers of the 1-oxide, 1,3-dioxide and 1,1,3-trioxide, respectively, of 2-benzyl-1,3,2-benzodithiazole have been isolated by chiral liquid chromatography. The rate of racemization was found to be much higher for the monooxide as compared to the dioxide or trioxide. A first-order rate constant of 8.65 × 10-5 s-1 was calculated for the racemization of the 1-oxide in acetonitrile at 21°C. This corresponds to rate constants for the forward and reverse reactions in the enantiomerization process of 4.32 × 10-5 s-1 and a Gibbs' free activation energy of only 96.5 kJ mol-1 separating the enantiomers. The absolute configuration at the tricoordinated sulfur atom in the series of oxides was determined via an X-ray crystallographic structure determination of one of the diastereomeric 2-((S)-α-phenyl-ethyl)-1,3,2-benzodithiazole 1,3-dioxides.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- 1 3 2-benzodithiazole S-oxides
- Absolute configuration
- Chiral liquid chromatography
- Enantiomerization barriers
- Optical resolution
Publication and Content Type
- ref (subject category)
- art (subject category)
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