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Issue 19, 2009
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Synthesis and structural investigation of N-acyl selenophosphoramides

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Abstract

2-Amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane reacts with acyl chlorides (4-chlorobenzoyl chloride or pivaloyl chloride) yielding the respective N-acyl selenophosphoramides. These derivatives do not isomerise to the related selenocarbonyl imides. X-ray study of N-(4-chlorobenzoyl)-2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane indicates that the selenium atom is placed in the equatorial position. The next compound studied, N-pivaloyl-2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane, crystallises with both axial/equatorial conformers present in the asymmetric unit. Finally, 2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane is present in the solid state in the form with the selenium atom in the axial position. The results are presented together with X-ray structures of previously synthesised and described cyclic O-acyl monoselenophosphates.

Graphical abstract: Synthesis and structural investigation of N-acyl selenophosphoramides

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Publication details

The article was received on 16 Apr 2009, accepted on 08 Jul 2009 and first published on 07 Aug 2009


Article type: Paper
DOI: 10.1039/B907641G
Citation: Org. Biomol. Chem., 2009,7, 4095-4100
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    Synthesis and structural investigation of N-acyl selenophosphoramides

    G. Cholewinski, J. Chojnacki, J. Pikies and J. Rachon, Org. Biomol. Chem., 2009, 7, 4095
    DOI: 10.1039/B907641G

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