Ethyl ester and silyl ester of imidodiphosphate: An alternative route to access phosphorus-nitrogen-phosphorus bonds via Staudinger reaction

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2018-03-25 DOI:10.1002/hc.21413

Jia En Low, Joëlle Levalois-Grützmacher

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.

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氨基二磷酸乙酯和硅基酯:通过Staudinger反应获得磷-氮-磷键的另一种途径

本文提出了另一种合成途径，通过磷酸酯中间体(1)和Staudinger反应得到四乙基亚胺二磷酸(EtO)2P(O)NH(O)P(OEt)2(3)及其硅酯衍生物四甲基(三甲基硅基)亚胺二磷酸(Me3SiO)2P(O)NH(O)P(OSiMe3)2(4)。与以前的方法相比，这种合成路线更简单，原子效率更高，能量成本更低。此外，得到的最终化合物收率更高，纯度更高。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.