Abstract
Aryl N-aroxycarbonyltrichloroacetimidates (Ar = Ph, 4-FC6H4) react with diphenylphosphinite according to the scheme of the aza-Perkow reaction to give the corresponding aryl N-(1-aroxy-2,2-dichloro-vinyl)-N-diphenylphosphinoylcarbamates. The structure of one of these compounds was confirmed by single crystal X-ray diffraction analysis. In the case of electron-accepting substituents (Ar = 4-O2N6H4), the primary product undergoes mild β-elimination to give nitrophenyl diphenylphosphinate and 1-nitrophenoxy-2,2-dichlorovinyl isocyanate. The reaction of trichloroacetimidates with triethyl phosphite yields a mixture of O- and N-phosphorylation products.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Sinitsa, A.D., Krishtal’, B.C., and Kal’chenko, V.I., Dokl. Akad. Nauk Ukr. SSR, Ser. B, 1979, no. 5, p. 357.
Sinitsya, O.A., Kolotilo, M.V., and Onis’ko, P.P., Ukr. Khim. Zh., 1998, vol. 64, no.5, p. 47.
Rassukanaya, Yu.V., Sizonenko, Ya.A., Sinitsa, A.A., Boiko, V.I., Podoprigorina, A.A., and Onys’ko, P.P., Zh. Obshch. Khim., 2002, vol. 72, no.11, p. 1798.
Boiko, V.I., Sinitsa, A.A., and Onys’ko, P.P., Zh. Obshch. Khim., 1999, vol. 69, no.12, p. 1966.
Boiko, V.I., Cand. Sci. (Chem.) Dissertation, Kiev, 1990.
Vovk, M.V., Bol’but, A.V., Lebed’, P.S., and Boiko, V.I., Khim. Geterotsikl. Soedin., 2004, no. 1, p. 102.
Kolotilo, N.V., Sinitsa, A.A., and Onys’ko, P.P., Izv. Ross. Akad. Nauk, Ser Khim., 1998, no. 10, p. 2101.
Bauermeister, S., Modro, T.A., and Zwierzak, A., Heteroatom Chem., 1993, vol. 4, no.1, p. 11.
Bauermeister, S. and Modro, T.A., Phosphorus, Sulfur, Silicon, 1992, vol. 72, no.1, p. 201.
Onys’ko, P.P., Zh. Obshch. Khim., 1999, vol. 69, no.1, p. 158.
Pudovik, A.N., Batyeva, E.S., and Al’fonsov, V.A., Phosphorus, Sulfur, Silicon, 1990, vol. 49/50, no. 1/4, p. 211.
Onys’ko, P.P., Kolodka, T.V., Kolotilo, N.V., Kudryavtsev, A.A., and Sinitsa, A.D., Zh. Obshch. Khim., 1994, vol. 64, no.3, p. 396.
Naumov, V.A. and Vilkov, L.V., Molekulyarnye struktury fosfororganicheskikh soedinenii (Molecular Structures of Organophosphorus Compounds), Moscow: Nauka, 1986.
Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Tailor, R., J. Chem. Soc., Perkin Trans. 2, 1987, no. 12, p. S1.
Burke-Laing, M. and Laing, M., Acta Crystallogr., Sect. B, 1976, vol. 32, no.12, p. 3216.
Alder, R.W., Goode, N.C., King, T.J., Mellor, J.M., and Miller, B.W., J. Chem. Soc., Chem. Commun., 1976, no. 5, p. 173.
Watkin, D.J., Prout, C.K., Carruthers, J.R., and Betteridge, P.W., CRYSTALS, issue 10, Chemical Crystallography Laboratory, Univ. of Oxford, 1996.
Carruthers, J.R. and Watkin, D.J., Acta Crystallogr., Sect. A, 1979, vol. 35, no.3, p. 698.
North, A.C.T., Phillips, D.C., and Mathews, F.S., Acta Crystallogr., Sect. A, 1968, vol. 24, no.2, p. 351.
Haake, P. and Hurst, G., J. Am. Chem. Soc., 1996, vol. 88, no.11, p. 2544.
Author information
Authors and Affiliations
Additional information
Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 11, 2004, pp. 1797–1803.
Original Russian Text Copyright © 2004 by Rassukanaya, Onys’ko, Sinitsa, Bol’but, Chernega.
Rights and permissions
About this article
Cite this article
Rassukanaya, Y.V., Onys’ko, P.P., Sinitsa, A.D. et al. Reactions of N-aroxycarbonyltrichloroacetimidates with nucleophilic phosphorus derivatives. Russ J Gen Chem 74, 1673–1678 (2004). https://doi.org/10.1007/s11176-005-0082-8
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11176-005-0082-8