References
- Michaelis , C. A. A. 1915 . Liebigs Ann. Chem. , 407 : 290
- Timperley , O. M. , Bird , M. , Broderick , J. F. , Holden , I. , Morton , I. J. and Waters , M. J. 2000 . J.Fluorine Chem. , 104 : 215
- Timperley , C. M. , Morton , I. J. , Waters , M. J. and Yarwood , J. L. 1999 . J.Fluorine Chem. , 96 : 95
- Timperley , C. M. , Broderick , J. F. , Holden , I. , Morton , I. J. and Waters , M. J. 2000 . J.Fluorine Chem. , 106 : 43
- Timperley , O. M. , Holden , I. , Morton , I. J. and Waters , M. J. 2000 . J.Fluorine Chem. , 106 : 153
- Timperley , C. M. and Waters , M. J. 2001 . Chem. Commun. , 9 : 797
- Henne , A. L. and Stewart , J. J. 1955 . J. Am. Chem. Soc. , 77 : 1901
- Reid , T. S. 1956 . Chem. Abs. , 50 : 2661f
- Gibbs , D. E. and Larsen , C. 1984 . Synthesis , : 410
- Markovskii , L. N. , Solov'ev , A. V. , Pashinnik , V. E. and Shermolovich , Yu G. 1980 . Zh. Obshch. Khim. (English translation) , 50 : 644
- Timperley , C. M. and Waters , M. J. 2001 . J.Fluorine Chem. , 109 : 103
- Henne , A. L. and Stewart , J. J. 1955 . J. Am. Chem. Soc. , 77 : 1901 Base dissociation constants were taken from, A CF3 group affects the basicity of the NH2 group adversely by a factor of 105 when separated by a single CH2 group. The data illustrates the strong inductive effect of the trifluoroethyl group; the reduced donor ability of the nitrogen atom in CF3CH2NH2 probably arises from some rehybridisation (greater s character of orbitals containing the electrons not involved in s bonds)
- Mochalina , K. P. , Dyatkin , B. L. and Knunyants , I. L. 1966 . Izv. Akad. Nauk. SSSR, Ser. Khim. , : 2188 *The preparation of diethyl N-(perfluoro-t-butyl) phosphoramidate (EtO)2P(O)NHC-(CF3)3 6 was first outlined in a short communication and reported later with experimental details. Refer to the English translations:
- Markovskii , L. N. , Solov'ev , A. V. , Pashinnik , V. K. and Shermolovich , Yu G. 1980 . Zh. Obshch. Khim. (English translation) , 50 : 644 *The study of heavily halogenated phosphorus molecules, such as bis(trichloroethyl) phosphoramidates, has been neglected. The amidate (CCl3CH2O)2P(O)NHPh, a white solid that melts between 135-136?C, was made by treatment of the chloridate with aniline. See
- Timperley , C. M. and Waters , M. J. 2001 . J.Fluorine Chem. , 109 : 103 *An analysis of the effects of fluorination on the boiling points of phosphoryl compounds appears in
- Dyatkin , B. L. , Mochalina , K. P. , Konstantinov , Yu S. , Sterlin , S. R. and Knunyants , I. L. 1967 . Izv. Akad. Nauk. SSSR, Ser. Khim. , : 2200 The related compound, diphenyl N-hexafluoroisopropyl phosphoramidate (PhO)2P(O)NHCH(CF3)2, a solid with a melting point of 173-174°C, was made in 57% yield by treating Cl2P(O)NHCH(CF3)2 with two molar equivalents of sodium phenoxide. See the English translation of
- Kozlov , K. S. , Kisilenko , A. A. , Sedlov , A. I. and Kirsanov , A. V. 1967 . Zh. Obshch, Khim. , 37 : 1528