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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


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1865-7117
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Volume 64, Issue 11-12

Issues

A Triple Newman-Kwart Rearrangement at a Fully Substituted Benzene Ring

Hubert Theil
  • Fakultät für Chemie, Universität Bielefeld, Universitätsstr. 25, D-33615 Bielefeld, Germany
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Roland Fröhlich
  • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität D-Münster, Corrensstr. 40, 48149 Münster, Germany
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Thorsten Glaser
Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-2009-11-1250

The Newman-Kwart rearrangement of O-thiocarbamates to S-thiocarbamates is a versatile method for the conversion of phenols into thiophenols. The triple rearrangement of the O-trithiocarbamate 2,4,6-triacetyl-1,3,5-tri-(dimethylthiocarbamoyloxy)benzene (2) to the S-trithiocarbamate 2,4,6- triacetyl-1,3,5-tri-(dimethylthiocarbamoylthio)benzene (3) is performed, which is unprecendented for fully substituted benzene rings. The synthesis and characterization of the O-trithiocarbamate 2 and the S-trithiocarbamate 3 including the single-crystal X-ray structure analysis of compound 3 are presented

Graphical Abstract

A Triple Newman-Kwart Rearrangement at a Fully Substituted Benzene Ring

A Triple Newman-Kwart Rearrangement at a Fully Substituted Benzene Ring

Keywords : Newman-Kwart Rearrangement; Thiocarbamates; Thiols

About the article

Received: 2009-09-16

Published Online: 2014-06-02

Published in Print: 2009-12-01


Citation Information: Zeitschrift für Naturforschung B, Volume 64, Issue 11-12, Pages 1633–1638, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2009-11-1250.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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