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Chiral sulfur‐containing structures: Selected synthetic and structural aspects

Chiral sulfur‐containing structures: Selected synthetic and structural aspects Synthetic procedures applied for the preparation of a new diastereomerically pure sulfinate and amidosulfite and a few enantiomerically pure sulfinyl derivatives, including sulfoxides functionalized with a perfluorocumyl substituent, are presented. Attempts to polymerize optically active 2‐(3‐thienyl)ethyl p‐tolyl sulfoxide are also mentioned. Mechanistic and stereochemical aspects of the presented protocols are discussed. Structural studies, which include the X‐ray, circular dichroism, and vibrational circular dichroism‐‐based determinations of the absolute configurations at the stereogenic sulfur atoms and calculations of conformational equilibria for a few model sulfur‐containing compounds are also described. The use of optically active t‐butylphenylthiophosphinic acid as a chiral solvating agent is illustrated. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:527–536, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20335 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

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References (37)

Publisher
Wiley
Copyright
Copyright © 2007 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.20335
Publisher site
See Article on Publisher Site

Abstract

Synthetic procedures applied for the preparation of a new diastereomerically pure sulfinate and amidosulfite and a few enantiomerically pure sulfinyl derivatives, including sulfoxides functionalized with a perfluorocumyl substituent, are presented. Attempts to polymerize optically active 2‐(3‐thienyl)ethyl p‐tolyl sulfoxide are also mentioned. Mechanistic and stereochemical aspects of the presented protocols are discussed. Structural studies, which include the X‐ray, circular dichroism, and vibrational circular dichroism‐‐based determinations of the absolute configurations at the stereogenic sulfur atoms and calculations of conformational equilibria for a few model sulfur‐containing compounds are also described. The use of optically active t‐butylphenylthiophosphinic acid as a chiral solvating agent is illustrated. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:527–536, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20335

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 2007

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