1
678
RASSUKANAYA et al.
Aryl N-diphenylphosphinoyl-N-(1-aroxy-2,2-di-
2. Sinitsya, O.A., Kolotilo, M.V., and Onis’ko, P.P., Ukr.
Khim. Zh., 1998, vol. 64, no. 5, p. 47.
chlorovinyl)carbamates Xa and Xc. To a solution of
imidate Ia or Ic in benzene, an equimolar amount of
ethyl diphenylphosphinite was added at 5 C. On the
next day, the solvent was evaporated and the residue
was crystallized from benzene.
3
. 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.
4
5
. Boiko, V.I., Sinitsa, A.A., and Onys’ko, P.P., Zh.
Obshch. Khim., 1999, vol. 69, no. 12, p. 1966.
Phenyl N-diphenylphosphinoyl-N-(1-phenoxy-
2
1
1
6
3
,2-dichlorovinyl)carbamate Xa. Yield 66%, mp
. Boiko, V.I., Cand. Sci. (Chem.) Dissertation, Kiev,
1
52 153 C. IR spectrum (KBr), , cm : 1280 (P=O),
1
990.
1
750 (C=O). H NMR spectrum (CDCl ), , ppm:
3
3
1
6. Vovk, M.V., Bol’but, A.V., Lebed’, P.S., and Boi-
ko, V.I., Khim. Geterotsikl. Soedin., 2004, no. 1,
p. 102.
.71 7.98 m. P NMR spectrum (CDCl3), P, ppm:
0.00. 13C NMR spectrum (CDCl ), , ppm: 117.2 d
3
3
(
[
(
1C, CCl , J 5 Hz); 118.8 s (2C) and 121.0 s (2C)
2 CP
2
2
C (PhOC)=, C (PhOCO)]; 124.4 s (1C) and 126.3 s
1C) [C (PhOC)=, C (PhOCO)]; 129.7 d (2C, CP,
7. Kolotilo, N.V., Sinitsa, A.A., and Onys’ko, P.P., Izv.
Ross. Akad. Nauk, Ser Khim., 1998, no. 10, p. 2101.
4
4
1
JCP 129 Hz); 139.4 s (1C) and 151.1 d (1C, CN,
8. Bauermeister, S., Modro, T.A., and Zwierzak, A., He-
teroatom Chem., 1993, vol. 4, no. 1, p. 11.
2
C=O, J 6 Hz); 149.9 s (1C) and 154.0 s (1C)
CP
1
1
[
(
C (PhOC)=, C (PhOCO)]; 120.96 s (2C), 128.5 d
4C, J 7.2 Hz), 129.4 d (2C, J 8.2 Hz), 131.7 d (2C,
9
. Bauermeister, S. and Modro, T.A., Phosphorus, Sulfur,
Silicon, 1992, vol. 72, no. 1, p. 201.
J 11 Hz), 132.3 (1C), 132.4 (1C), 137.8 (2C) (Ph).
The signals of the carbon atoms not bonded to hydro-
10. Onys’ko, P.P., Zh. Obshch. Khim., 1999, vol. 69,
1
3
gen were identified by recording the C NMR spectra
under the conditions of APT experiment. Found, %:
no. 1, p. 158.
1
1
1
1. Pudovik, A.N., Batyeva, E.S., and Al’fonsov, V.A.,
Phosphorus, Sulfur, Silicon, 1990, vol. 49/50,
no. 1/4, p. 211.
C 61.83; H 3.88; Cl 13.53; N 2.69; P 5.88. C H
2
7
20
Cl NO P. Calculated, %: C 61.84; H 3.84; Cl 13.52;
2
4
N 2.67; P 5.90.
-Fluorophenyl N-diphenylphosphinoyl-N-[1-
4-fluorophenoxy)-2,2-dichlorovinyl]carbamate Xc.
Yield 63%, mp 115 117 C. IR spectrum (KBr), ,
2. Onys’ko, P.P., Kolodka, T.V., Kolotilo, N.V., Kud-
ryavtsev, A.A., and Sinitsa, A.D., Zh. Obshch. Khim.,
1994, vol. 64, no. 3, p. 396.
4
(
3. Naumov, V.A. and Vilkov, L.V., Molekulyarnye
struktury fosfororganicheskikh soedinenii (Molecular
Structures of Organophosphorus Compounds), Mos-
cow: Nauka, 1986.
1
1
cm : 1280 (P=O), 1750 (C=O). H NMR spectrum
3
1
(
(
CDCl ), , ppm: 6.66 7.96 m. P NMR spectrum
CDCl3), P, ppm: 29.60. F NMR spectrum (CDCl3),
F, ppm: 112.1 (1F, FC H OCO), 114.8 (1F,
3
1
9
6
4
1
1
4. 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.
FC H OC=). Found, %: C 57.49; H 3.18; Cl 12.47;
6
4
N 2.53; P 5.38. C H Cl F NO P. Calculated, %: C
2
7
18
2
2
4
5
7.87; H 3.23; Cl 12.65; N 2.50; P 5.53.
-Nitrophenyl diphenylphosphinate XI. Yield
9%, mp 149 150 C (published data [20]: 149
5. Burke-Laing, M. and Laing, M., Acta Crystallogr.,
Sect. B, 1976, vol. 32, no. 12, p. 3216.
4
6
1
1
[
1
1
1
3
50 C).
C NMR spectrum (CDCl ), C, ppm:
16. 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.
3
2
3
21.14 d [C (C H NO ),
J 5.3 Hz], 125.58 s
6
4
2
CP
3
2
2
C (C H NO )], 128.81 d [C (Ph), J 13.7 Hz],
6 4 2 CP
1
3
3
29.83 d (CP, J 140 Hz), 131.63 d [C (Ph), J
0.9 Hz], 132.98 d [C (Ph), J 3.5 Hz], 144.27 s
17. Watkin, D.J., Prout, C.K., Carruthers, J.R., and Bette-
ridge, P.W., CRYSTALS, issue 10, Chemical Crystal-
lography Laboratory, Univ. of Oxford, 1996.
CP
CP
4
4
CP
2
31
(
CNO ), 155.95 d (COP, J 7.8 Hz). P NMR spec-
2 CP
trum (CDCl3), P, ppm: 32.9.
18. Carruthers, J.R. and Watkin, D.J., Acta Crystallogr.,
Sect. A, 1979, vol. 35, no. 3, p. 698.
REFERENCES
1
9. North, A.C.T., Phillips, D.C., and Mathews, F.S., Acta
Crystallogr., Sect. A, 1968, vol. 24, no. 2, p. 351.
1
. Sinitsa, A.D., Krishtal’, B.C., and Kal’chenko, V.I.,
Dokl. Akad. Nauk Ukr. SSR, Ser. B, 1979, no. 5,
p. 357.
20. Haake, P. and Hurst, G., J. Am. Chem. Soc., 1996,
vol. 88, no. 11, p. 2544.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 11 2004