Substitution of Chloride Ion in Bis(2-Chloroethyl) Sulfide (HD) by Various Oxygen Anions

Abstract

The chemical warfare agent bis(2-chloroethyl) sulfide, (HD: Mustard Gas) reacts with the potassium salts of benzohydroxamic acid, phenol and 2,3- butanedione monoxime in aqueous ethanol to give solid crystalline products in greater than 80% yields. These products have been isolated, purified and characterized. Analysis shows that both chloride atoms of HD have been substituted by the respective oxygen anion group in the products. These results indicate that, in this system, nucleophilic substitution of mustard is preferred over the elimination mechanism.

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1990
Accession Number
ADA224001

Entities

People

  • Edward J. Dunn
  • Raynor K. Miller

Organizations

  • Defence Research and Development Canada

Tags

DTIC Thesaurus Topics

  • Abstracts
  • Agreements
  • Alcohols
  • Chemical Warfare
  • Chemical Warfare Agents
  • Chemistry
  • Chromatography
  • Detectors
  • Elimination
  • Gas Chromatography
  • Hydrolysis
  • Mustard Agents
  • National Security
  • Optical Materials
  • Resonance
  • Spectra
  • Substitution Reactions

Fields of Study

  • Chemistry

Readers

  • Analytical Chemistry
  • Organic Chemistry