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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 7, pp 733–737 | Cite as

Structures and reactivities of benzo-1,2,3-dithiazolium salts and their selenium analogs

  • Yu. I. Akulin
  • M. M. Gel'mont
  • B. Kh. Strelets
  • L. S. Éfros
Article

Abstract

A number of benzo-1,2,3-dithiazolium chlorides (I) and their selenium analogs — benzo-1,2,3-thiaselenazolium, benzo-2,1,3-thiaselenazolium, and benzo-1,2,3-diselenazolium salts — were synthesized. The electronic structures and reactivities of the I cation and salts I–IV are discussed on the basis of a quantum-chemical calculation of cation I and the PMR spectra of salts I–IV. Successive substitution of the sulfur atoms in the I cation by selenium atoms, particularly in the 2 position, substantially increases the degree of transfer of positive charge to the condensed benzene ring. The trend of the nucleophilic reactivities of 6-methoxy derivatives of salts I–IV in the reaction with aromatic amines is the same as the trend of the degree of localization of the positive charge in the 6 position.

Keywords

Sulfur Chloride Benzene Organic Chemistry Selenium 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • Yu. I. Akulin
    • 1
  • M. M. Gel'mont
    • 1
  • B. Kh. Strelets
    • 1
  • L. S. Éfros
    • 1
  1. 1.Leningrad BranchDesign Scientific-Research Institute of Synthetic FibersLeningrad

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