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Imines and Derivatives. Part 20. N-Phosphinoyloxaziridines: Synthesis and Structural Characterisation by Nuclear Magnetic Resonance Spectroscopy and a Crystal Structure of 3-(4-Chlorophenyl)-2-(diphenylphosphinoyl)oxaziridine

DOI: 10.1039/P29880001145

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1145 - 1150 (1988)

Update date:2022-07-29

Topics: Synthesis   Crystal structure   Imines   Derivatives   Structural characterization   Nuclear magnetic resonance spectroscopy  

Authors:

Boyd, Derek R.Boyd, Derek R.

Malone, John F.Malone, John F.

McGuckin, M. RosaleenMcGuckin, M. Rosaleen

Jennings, W. BrianJennings, W. Brian

Rutherford, MarkRutherford, Mark

Saket, Barahman M.Saket, Barahman M.

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Article abstract of DOI:10.1039/P29880001145

The preparation of a new class of oxaziridines containing an N-phosphinoyl group is described.The compounds were obtained by peroxyacid oxidation of N-phosphinoyl imines under basic or neutral conditions, and characterised by n.m.r. spectroscopy.Revelant 2JPC, 3JPH, and 1JCH coupling constants are reported.An X-ray structure analysis of the title compound establishes that the 2-diphenylphosphinoyl group is trans to the 3-aryl ring.The P-N bond length (1.76 Angstroem) is abnormally high for an aminophosphorus(v) compound and the nitrogen atom is pyramidal (ΣN=280 deg).This geometry is interpreted in terms of an unusually low degree of ?-bonding between nitrogen and phosphorus due to the high s-character of the nitrogen lone pair.

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