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J Am Chem Soc. 2013 Dec 26;135(51):19131-4. doi: 10.1021/ja4115693. Epub 2013 Dec 11.

Phosphinecarboxamide: a phosphorus-containing analogue of urea and stable primary phosphine.

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  • 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.


Reactions of the 2-phosphaethynolate anion (PCO(-), 1) with ammonium salts quantitatively yielded phosphinecarboxamide (PH2C(O)NH2, 2). The molecular structure and chemical properties of 2 were studied by single-crystal X-ray diffraction and multielement NMR spectroscopy. This phosphorus-containing analogue of urea is a rare example of an air-stable primary phosphine.

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