Issue 19, 2009
From the journal:

Organic & Biomolecular Chemistry

Synthesis and structural investigation of N-acyl selenophosphoramides†

Grzegorz Cholewinski,a   Jaroslaw Chojnacki,b   Jerzy Pikiesb  and  Janusz Rachon*a  

* Corresponding authors

a Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk

b Department of Inorganic Chemistry, Chemical Faculty, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk

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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Article information

DOI
https://doi.org/10.1039/B907641G
Article type
Paper
Submitted
16 Apr 2009
Accepted
08 Jul 2009
First published
07 Aug 2009

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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