Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi
{"title":"带有不同烷基氨基的新型高氟化磷酰胺的合成与表征","authors":"Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi","doi":"10.1080/00397911.2024.2382784","DOIUrl":null,"url":null,"abstract":"<div><p>Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R<sub>F</sub>O)<sub>2</sub>P(O)NHR (R = CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>3</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>4</sub>-CH<sub>3</sub>, CH(CH<sub>3</sub>)<sub>2</sub>, C<sub>6</sub>H<sub>11</sub>, CH<sub>2</sub>CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub>, CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub> or C<sub>6</sub>H<sub>5</sub>; R<sub>F</sub> = CH<sub>2</sub>CF<sub>3</sub>, CH<sub>2</sub>C<sub>2</sub>F<sub>5</sub> or CH<sub>2</sub>CH<sub>2</sub>C<sub>6</sub>F<sub>13</sub>) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H<sub>2</sub>O<sub>2.</sub>This method was chosen out of various literature common methods, which were thoroughly investigated using <sup>31</sup>P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (<sup>1</sup>H,<sup>13</sup>C,<sup>31</sup>P, and <sup>19</sup>F) NMR, IR, and HRMS techniques.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups\",\"authors\":\"Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi\",\"doi\":\"10.1080/00397911.2024.2382784\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R<sub>F</sub>O)<sub>2</sub>P(O)NHR (R = CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>3</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>4</sub>-CH<sub>3</sub>, CH(CH<sub>3</sub>)<sub>2</sub>, C<sub>6</sub>H<sub>11</sub>, CH<sub>2</sub>CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub>, CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub> or C<sub>6</sub>H<sub>5</sub>; R<sub>F</sub> = CH<sub>2</sub>CF<sub>3</sub>, CH<sub>2</sub>C<sub>2</sub>F<sub>5</sub> or CH<sub>2</sub>CH<sub>2</sub>C<sub>6</sub>F<sub>13</sub>) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H<sub>2</sub>O<sub>2.</sub>This method was chosen out of various literature common methods, which were thoroughly investigated using <sup>31</sup>P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (<sup>1</sup>H,<sup>13</sup>C,<sup>31</sup>P, and <sup>19</sup>F) NMR, IR, and HRMS techniques.</p></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-08-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0039791124000699\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000699","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups
Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (RFO)2P(O)NHR (R = CH2CH2CH3, (CH2)3CH3, (CH2)4-CH3, CH(CH3)2, C6H11, CH2CH2-C6H5, CH2-C6H5 or C6H5; RF = CH2CF3, CH2C2F5 or CH2CH2C6F13) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H2O2.This method was chosen out of various literature common methods, which were thoroughly investigated using 31P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (1H,13C,31P, and 19F) NMR, IR, and HRMS techniques.
期刊介绍：
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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