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Original Articles

THE DIHYDROPHENOPHOSPHAZINE RING SYSTEM. 2. THE REACTION OF PHOSPHORUS TRIHALIDES WITH HALO-SUBSTITUTED AND STERICALLY HINDERED DIARYLAMINES

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Pages 269-272 | Received 22 Mar 1980, Published online: 19 Dec 2006

References

  • Jenkins , R. N. and Freedman , L. D. 1975 . J. Org. Chem. , 40 : 766 For paper 1 in this series, see
  • Butler , J. R. 1977 . North Carolina State University . Abstracted from the M.S. theses of and Freeman H., S., North Carolina State University, 1978
  • Michaelis , A. and Schenk , A. 1890 . Justus Liebigs Ann. Chem. , 260 : 1
  • Häring , M. 1960 . Helv. Chim. Acta , 43 : 1826
  • Jenkins , R. N. , Freedman , L. D. and Bordner , J. 1971 . Chem. Commun. , : 1213
  • Bokanov , A. I. and Stepanov , B. I. 1977 . Usp. Khim. , 46 : 1625 A. N. Smirnov, L. A. Yagodina, V. M. Orlov, O. G. Piskunova, A. I. Bokanov, and B. I. Stepanov, Zh. Obshch. Khim., 47, 2468 (1977); M. K. Polievktov, A. I. Bokanov, O. G. Piskunova, and B. I. Stepanov, Zh. Obshch. Khim., 47, 2730 (1977); O. G. Piskunova, A. I. Bokanov, and B. I. Stepanov, Zh. Obsch. Khim., 48, 1312 (1978); O. G. Piskunova, L. A. Yagodina, B. A. Korolev, A. I. Bokanov, and B. I. Stepanov, Zh. Obsch. Khim., 48, 1316 (1978); D. Hellwinkel, W. Schenk, and W. Blaicher, Chem. Ber., 111, 1798 (1978)
  • Only a fraction of the phosphine oxide actually formed was isolated as such. Most of it was converted (by oxidation with sodium hydroxide in aqueous ethanol) to the more easily isolated phosphinic acid; see also ref. 1
  • Phosphorus tribromide rather than the trichloride was used in this reaction in order to avoid the possibility of replacement of the ring bromine atoms by chlorine. We first ascertained that the interaction of diphenylamine and phosphorus tribromide (followed by treatment of the reaction mixture with water) leads to the same products in about the same yields as when the trichloride is used
  • Sollott , G. P. and Peterson , W. R. Jr. 1969 . J. Organomet. Chem. , 19 : 143 The interaction of diphenylamine and phosphorus trichloride at room temperature yields diphenylphosphoramidous dichloride, Ph2NPCl2; cf. We have previously noted1 that this type of compound is probably an intermediate in the high temperature reaction between a diarylamine and phosphorus trichloride
  • Melting points were determined with a Mel-Temp capillary melting point apparatus and are uncorrected. IR spectra were obtained with either a Beckman IR 8 or Perkin-Elmer Model 521 spectrophotometer. Mass spectra were taken at 70 eV with a solid injection probe on an Associated Electrical Industries MS12, a Varian MAT, or a Varian MAT 731 mass spectrometer. Elemental analyses were performed by either Integral Microanalytical Laboratories, Raleigh, N. C. or Galbraith Laboratories, Inc., Knoxville, Tenn. The reactions between the diarylamines and phosphorus trihalides were carried out in “resin reaction kettles” as previously described.1
  • Freeman , H. S. , Butler , J. R. and Freedman , L. D. 1978 . J. Org. Chem. , 43 : 4975
  • Sen , A. B. and Sen Gupta , A. K. 1957 . J. Indian Chem. Soc. , 34 : 413
  • Smith , P. A. S. and Kelenda , N. W. 1958 . J. Org. Chem. , 23 : 1599
  • Koshkin , L. V. , Basaev , R. M. , Fedorina , N. T. , Basaeva , N. N. and Musabekov , Yu. S. 1968 . Zh. Org. Khim. , 4 : 2175
  • Jones , R. E. and Wasserman , D. U.S. Patent . 3 065 251 . Nov. 20, 1962 . Chem. Abstr., 59, 11530 (1963)

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