Efficient oxidation of sulfur mustard and its simulants using N-tert-butyl-N-chlorocyanamide

Synthetic Communications

Volumn 36, Issue 16, 2006, Pages 2385-2388

  Kumar, Vinod ^a   Kaushik, M P ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Decontamination; N tert butyl N chlorocyanamide; Simulants; Sulfoxides; Sulfur mustard

Indexed keywords

CYANAMIDE; MUSTARD GAS; N TERT BUTYL N CHLOROCYANAMIDE; SULFOXIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; OXIDATION; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SIMULATION; TEMPERATURE;

EID: 33747596169     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600640370     Document Type: Article

References (15)

1. (a) Papirmeister, B.; Feister, A. J.; Robinson, S. I.; Ford, R. D. CRC Press: Boca Raton, FL, 1991; p. 359;
2. (b) Pechura, C. M.; Rail, D. P. National Academy Press: Washington, DC, 1993; p. 428.
3. (a) Yang, Y. C.; Baker, J. A.; Ward, J. R. Decontamination of chemical warfare agents. Chem. Rev. 1992, 92, 1729, and references therein;
4. (b) Dubey, D. K.; Malhotra, R. C.; Vaidyanathaswamy, R.; Vijayraghvan, R. Reaction of bis(2-chloroethyl)sulfide with N,N′-dichlorobis(2,4,6- trichlorophenyl)urea. J. Org. Chem. 1999, 64, 8031.
5. (a) Leblanc, A.; Fosset, L.; Magnaud, G.; Desgranges, M.; Sentenac-Roumanou, H.; Lion, C.; Charvy, C.; Mohri, A. New decontaminants: Oxidative degradation of sulfur mustard and analogs: 2-Chloroethyl phenyl sulfide by potassium monopersulfate. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 79, 141;
6. (b) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimotoa, T. A mild, inexpensive, and convenient synthesis of sulfoxides by the oxidation of sulfides with calcium hypochlorite and moist alumina. Synthesis 1997, 1161.
7. Yang, Y. C.; Szafraniec, L. L.; Beaudry, W. T.; Davis, F. A. A comparison of the oxidative reactivities of mustard (2,20-dichlorodiethyl sulfide) and bivalent sulfides. J. Org. Chem. 1990, 55, 3664.
8. 2. Coord. Chem. Rev. 1992, 117, 185.
9. Delmas, G.; Desgranges, M.; Lion, C.; Magnaud, M.; Sentenac-Roumanou, H. Fr. Pat. C2676368, 1991.
10. Ganzago, F.; Perez, E.; Rico-Lattes, I.; Lattes, A. New microemulsions for oxidative decontamination of mustard gas analogues and polymer-thickened half-mustard. New. J. Chem. 2001, 25, 151.
11. Vorontsov, A. V.; Lion, C.; Savinov, E. N.; Smirniotis, P. G. Pathways of photocatalytic gas phase destruction of HD simulant 2-chloroethyl ethyl sulfide. J. Catal. 2003, 220, 414.
12. 2/air-based oxidation of 2-chloroethyl-ethyl sulfide at ambient temperature. J. Mol. Catal. A. 2003, 197, 283.
13. (a) Kumar, V.; Kaushik, M. P. N-tert-Butyl-N-chlorocyanamide: An efficient reagent for the preparation of gem-chloronitroso compounds. Tetrahedron Lett. 2005, 46, 8121;
14. (b) Kumar, V.; Kaushik, M. P. A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide. Tetrahedron Lett. 2006, 47, 1457-1460.
15. Neale, R. S.; Marcus, N. L. Chemistry of nitrogen radicals, IX: Reactions of N-halocyanamides and N-halosulfonamides. J. Org. Chem. 1969, 34, 1808.