Synthesis and structural investigation of N-acyl selenophosphoramides

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (19), p.4095-4100
Main Authors: Cholewinski, Grzegorz, Chojnacki, Jaroslaw, Pikies, Jerzy, Rachon, Janusz
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - chemistry
Crystallography, X-Ray
Isomerism
Magnetic Resonance Spectroscopy
Phosphoramides
Phosphoric Acids - chemical synthesis
Phosphoric Acids - chemistry
Quantum Theory
Selenium - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b907641g