{"title":"Ethyl ester and silyl ester of imidodiphosphate: An alternative route to access phosphorus-nitrogen-phosphorus bonds via Staudinger reaction","authors":"Jia En Low, Joëlle Levalois-Grützmacher","doi":"10.1002/hc.21413","DOIUrl":null,"url":null,"abstract":"<p>We present herein an alternative synthesis route to obtain tetraethyl imidodiphosphate (EtO)<sub>2</sub>P(O)NH(O)P(OEt)<sub>2</sub> (<b>3</b>) and its silylester derivative tetrakis(trimethylsilyl) imidodiphosphate (Me<sub>3</sub>SiO)<sub>2</sub>P(O)NH(O)P(OSiMe<sub>3</sub>)<sub>2</sub> (<b>4</b>) involving a phosphorazidate intermediate (<b>1</b>) and the Staudinger reaction. Compared to previous methods, this synthesis route is simpler, more atom efficient, and energetically inexpensive. Moreover, the final compounds are obtained with larger yield and higher purity.</p>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2018-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21413","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hc.21413","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
We present herein an alternative synthesis route to obtain tetraethyl imidodiphosphate (EtO)2P(O)NH(O)P(OEt)2 (3) and its silylester derivative tetrakis(trimethylsilyl) imidodiphosphate (Me3SiO)2P(O)NH(O)P(OSiMe3)2 (4) involving a phosphorazidate intermediate (1) and the Staudinger reaction. Compared to previous methods, this synthesis route is simpler, more atom efficient, and energetically inexpensive. Moreover, the final compounds are obtained with larger yield and higher purity.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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