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Vos BW, Jenks WS. Evidence for a nonradical pathway in the photoracemization of aryl sulfoxides. J Am Chem Soc. 2002;124(11):2544-7doi: 10.1021/ja017228m.
Vos, B. W., & Jenks, W. S. (2002). Evidence for a nonradical pathway in the photoracemization of aryl sulfoxides. Journal of the American Chemical Society, 124(11), 2544-7. https://doi.org/10.1021/ja017228m
Vos, Brian W, and Jenks, William S. "Evidence for a nonradical pathway in the photoracemization of aryl sulfoxides." Journal of the American Chemical Society vol. 124,11 (2002): 2544-7. doi: https://doi.org/10.1021/ja017228m
Vos BW, Jenks WS. Evidence for a nonradical pathway in the photoracemization of aryl sulfoxides. J Am Chem Soc. 2002 Mar 20;124(11):2544-7. doi: 10.1021/ja017228m. PMID: 11890804.
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J Am Chem Soc. 2002 Mar 20;124(11):2544-7. doi: 10.1021/ja017228m.

Evidence for a nonradical pathway in the photoracemization of aryl sulfoxides.

Journal of the American Chemical Society

Brian W Vos, William S Jenks

Affiliations

  1. Department of Chemistry, Iowa State University, Ames, IA 50011-3111, USA.

PMID: 11890804 DOI: 10.1021/ja017228m

Abstract

Photolysis of (R(S),S(C))-1-deuterio-2,2-dimethylpropyl p-tolyl sulfoxide provides mainly (S(S),S(C))-1-deuterio-2,2-dimethylpropyl p-tolyl sulfoxide at low conversion, though the other two stereoisomers are formed to smaller extents. Thus, the predominant process leading to sulfur inversion yields only sulfur inversion, without inversion of the adjacent CHD stereogenic center. This is taken as evidence for a mechanism for photochemical epimerization of sulfoxides that does not involve homolytic alpha-cleavage chemistry.

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