Studies on Organophosphorus Compounds (LVII)——Radical Addition of Diphenyl (Diphenoxy) Phosphorus Chloride to Oximes——A New Synthetic Approach to-1-Aminoalkyl-Diphenylphosphine Oxides and Diphenyl-1-Aminoalkylphosphonates

Chem. J. Chinese Universities ›› 1992, Vol. 13 ›› Issue (9): 1206.

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Studies on Organophosphorus Compounds (LVII)——Radical Addition of Diphenyl (Diphenoxy) Phosphorus Chloride to Oximes——A New Synthetic Approach to-1-Aminoalkyl-Diphenylphosphine Oxides and Diphenyl-1-Aminoalkylphosphonates

YUAN Cheng-Ye¹, QI You-Mao¹, CHEN Guo-Fei¹, ZHAO Cheng-Xue²

1. Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai, 200032;
2. Huazhong University of Science and Technology, Department of Chemistry, Wuhan

Received:1991-07-07 Revised:1992-05-24 Online:1992-09-24 Published:1992-09-24

Abstract

Abstract: The reaction of diphenyl(phenoxy) phosphorus chlorides with oximes in the presence of triethylamine in a perhalogenated solvent CFCl₂CF₂Cl can serve as a new synthetic approach to 1-aminoalkyl diphenyl phosphine oxides or diphenyl 1-aminoalkylphosphonates with good or excellent yields under mild conditions.Direct EPRobservations of radical intermediates Ph₂＝O,PhCH＝N·originated from the homolytic scission of the unstable condensation product Ph₂PON＝CHPh in the first stage,and the spin adduct of Ph₂＝O to Ph₂PON＝CH-Ph,has revealed the first example of radical addition of phosphorus reagents to bonds.

Key words: Diphenylphosphorus chloride, Diphenoxyphosphorus chloride, 1-Aminoalkyl diphenylphosphine oxide, Radical addition, EPR

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YUAN Cheng-Ye, QI You-Mao, CHEN Guo-Fei, ZHAO Cheng-Xue. Studies on Organophosphorus Compounds (LVII)——Radical Addition of Diphenyl (Diphenoxy) Phosphorus Chloride to Oximes——A New Synthetic Approach to-1-Aminoalkyl-Diphenylphosphine Oxides and Diphenyl-1-Aminoalkylphosphonates[J]. Chem. J. Chinese Universities, 1992, 13(9): 1206.

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Studies on Organophosphorus Compounds (LVII)——Radical Addition of Diphenyl (Diphenoxy) Phosphorus Chloride to Oximes——A New Synthetic Approach to-1-Aminoalkyl-Diphenylphosphine Oxides and Diphenyl-1-Aminoalkylphosphonates

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