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-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.
Cholewinski
Grzegorz
G
Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, G. Narutowicza 11/12, 80-233, Gdansk.
Chojnacki
Jaroslaw
J
Pikies
Jerzy
J
Rachon
Janusz
J
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D063088:Phosphoramides; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D011789:Quantum Theory; D012643:Selenium / Q000737:chemistry*
D000577:Amides; D063088:Phosphoramides; D010756:Phosphoric Acids; C005438:phosphoramide; D012643:Selenium