Thierry Cassagne , Henri-Jean Cristau , Gérard Delmas , Michel Desgranges , Claude Lion , Gilbert Magnaud , Éliane Torreilles , David Virieux
{"title":"N,N-二异丙基-2-氨基乙基-氟苯硫磺酸盐与氧化剂的反应","authors":"Thierry Cassagne , Henri-Jean Cristau , Gérard Delmas , Michel Desgranges , Claude Lion , Gilbert Magnaud , Éliane Torreilles , David Virieux","doi":"10.1016/S1387-1609(01)01231-2","DOIUrl":null,"url":null,"abstract":"<div><p>The behaviour of <em>N,N</em>-diisopropyl-2-aminoethyl <em>p-</em>fluorobenzene thiosulfonate <strong>3</strong>, which may be considered as a weakly toxic chemical analogue of VX agent, was investigated against oxidising agents. As VX <strong>1</strong>, this compound exhibits the same tendency to give S–S bond cleavage. Its degradation by Curox® shows the formation of the <em>N-</em>oxide <strong>6</strong> which subsequently gives the sulfonate <strong>7</strong> by hydrolysis. The action of hydrogen peroxide, with or without boric acid, leads to the sulfinate <strong>4</strong> by S-S bond cleavage. Its oxidation gives sulfonate <strong>7</strong>. Finally, reactions of MMPP and <em>m-</em>CPBA afford sulfonate <strong>7</strong> but no intermediates are highlighted with these reagents.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 4","pages":"Pages 309-314"},"PeriodicalIF":0.0000,"publicationDate":"2001-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01231-2","citationCount":"1","resultStr":"{\"title\":\"Reactions of N,N-diisopropyl-2-aminoethylp-fluorobenzene thiosulfonate with oxidising agents\",\"authors\":\"Thierry Cassagne , Henri-Jean Cristau , Gérard Delmas , Michel Desgranges , Claude Lion , Gilbert Magnaud , Éliane Torreilles , David Virieux\",\"doi\":\"10.1016/S1387-1609(01)01231-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The behaviour of <em>N,N</em>-diisopropyl-2-aminoethyl <em>p-</em>fluorobenzene thiosulfonate <strong>3</strong>, which may be considered as a weakly toxic chemical analogue of VX agent, was investigated against oxidising agents. As VX <strong>1</strong>, this compound exhibits the same tendency to give S–S bond cleavage. Its degradation by Curox® shows the formation of the <em>N-</em>oxide <strong>6</strong> which subsequently gives the sulfonate <strong>7</strong> by hydrolysis. The action of hydrogen peroxide, with or without boric acid, leads to the sulfinate <strong>4</strong> by S-S bond cleavage. Its oxidation gives sulfonate <strong>7</strong>. Finally, reactions of MMPP and <em>m-</em>CPBA afford sulfonate <strong>7</strong> but no intermediates are highlighted with these reagents.</p></div>\",\"PeriodicalId\":100305,\"journal\":{\"name\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"volume\":\"4 4\",\"pages\":\"Pages 309-314\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2001-04-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01231-2\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1387160901012312\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1387160901012312","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Reactions of N,N-diisopropyl-2-aminoethylp-fluorobenzene thiosulfonate with oxidising agents
The behaviour of N,N-diisopropyl-2-aminoethyl p-fluorobenzene thiosulfonate 3, which may be considered as a weakly toxic chemical analogue of VX agent, was investigated against oxidising agents. As VX 1, this compound exhibits the same tendency to give S–S bond cleavage. Its degradation by Curox® shows the formation of the N-oxide 6 which subsequently gives the sulfonate 7 by hydrolysis. The action of hydrogen peroxide, with or without boric acid, leads to the sulfinate 4 by S-S bond cleavage. Its oxidation gives sulfonate 7. Finally, reactions of MMPP and m-CPBA afford sulfonate 7 but no intermediates are highlighted with these reagents.
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