1050
Russ.Chem.Bull., Int.Ed., Vol. 50, No. 6, June, 2001
Nenajdenko et al.
17
1-(2,2-Dichlorovinyl)-3-fluorobenzene (1r): nD 1.5685.
Found (%): C, 50.56; H, 2.79. C8H5Cl2F. Found (%): C, 50.30;
H, 2.64. IR, ν/cm1: 1620, 1590, 1240, 790. 1H NMR, δ: 6.76
(s, 1 H, CH=); 6.96 (dd, 1 H, Ar, J = 8.3 and 2.5 Hz);
7.167.31 (m, 3 H, Ar). 13C NMR, δ: 115.1 (Ar, J = 22.3 Hz);
115.4 (Ar); 122.3 (=CCl2); 124.6 (CH=); 127.4 (Ar,
J = 2.3 Hz); 129.9 (Ar, J = 8.4 Hz); 135.2 (Ar, J = 8.2 Hz);
162.6 (CF, J = 245 Hz).
References
1. J. Villieras, P. Perriot, and J. F. Normant, Synthesis,
1975, 458.
2. J. Villieras, C. Bacquet, and J. F. Normant, J. Organomet.
Chem., 1975, 97, 355.
3. P. Vinczer, S. Struhar, L. Novak, and C. Szantay, Tetra-
hedron Lett., 1992, 33, 683.
4. J. S. Yadav, V. Prahlad, and M. C. Chander, J. Chem. Soc.,
Chem. Commun., 1993, 137.
5. A. J. Speziale and K. W. Ratts, J. Am. Chem. Soc., 1962,
84, 854.
6. D. Seyferth and R. S. Marmor, J. Organomet. Chem., 1973,
59, 237.
1-(2,2-Dichlorovinyl)-2-fluorobenzene (1s): Found (%):
C, 50.42; H, 2.59. C8H5Cl2F. Found (%): C, 50.30; H, 2.64.
IR, ν/cm1: 1610, 1590, 1240, 850. 1H NMR, δ: 6.96 (s, 1 H,
CH=); 7.04 (ddd, 1 H, Ar, J = 9.9, 8.4, and 1.2); 7.12 (ddd,
1 H, Ar, J = 8.7, 7.7, and 1.2); 7.27 (m, 1 H, Ar); 7.76 (ddd,
1 H, Ar, J = 9.2, 7.7, and 1.5 Hz). 13C NMR, δ: 115.4 (Ar,
J
= 21.9 Hz); 121.1 (CH=, J = 5.9 Hz); 121.4 (Ar,
J = 12.7 Hz); 123.2 (Ar, J = 1.7 Hz); 123.9 (=CCl2, J = 3.7 Hz);
129.2 (Ar, J = 2.1 Hz); 130.1 (Ar, J = 8.4 Hz); 159.7 (CF,
J = 251 Hz).
7. R. Rabinowitz, J. Am. Chem. Soc., 1962, 84, 1312.
8. D. J. Burton and J. R. Greenwald, Tetrahedron Lett.,
1967, 1535.
2-(2,2-Dichlorovinyl)-4-nitrophenol (1t): m.p. 153155 °C
9. A. Merz, Angew. Chem., 1977, 89, 54.
(cf. lit. data:15 m.p. 153155 °C).
10. R. P. Gajewski, J. L. Jackson, N. D. Jones, J. K.
Swartzendruber, and J. B. Deeter, J. Org. Chem., 1989,
54, 3311.
11. Z. Wang, S. Campagna, G. Xu, M. E. Pierce, J. M.
Fortunak, and P. N. Confalone, Tetrahedron Lett., 2000,
41, 4007.
1,4-Bis(2,2-dichlorovinyl)benzene (1u): m.p. 7778 °C.
IR, ν/cm1: 1610. 1H NMR, δ: 6.75 (s, 2 H, CH=); 7.47 (s,
4 H, Ar). 13C NMR, δ: 122.5 (=CCl2); 128.6 (CH=); 129.4
(Ar); 134.1 (Ar). Found (%): C, 45.16; H, 2.40. C10H6Cl4.
Found (%): C, 44.82; H, 2.26.
1-(2,2-Dichlorovinyl)naphthalene (1v): m.p. 42 °C (cf. lit.
12. H. Tanaka, S. Yamashita, M. Yamanoue, and S. Torii,
J. Org. Chem., 1989, 54, 444.
data26: m.p. 42 °C).
20
3-(2,2-Dichlorovinyl)pyridine (1w): nD
1.5985 (cf. lit.
13. H. O. Krabbenhoft, J. Org. Chem., 1978, 43, 1305.
14. A. V. Shastin, V. N. Korotchenko, V. G. Nenaidenko, and
E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 1999, 2210
[Russ. Chem. Bull., 1999, 48, 2184 (Engl. Transl.)].
15. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and
E. S. Balenkova, Tetrahedron, 2000, 56, 6557.
16. K. Juhl, R. G. Hazell, and K. A. Jorgensen, J. Chem. Soc.,
Perkin Trans. 1, 1999, 16, 2293.
data27: nD20 1.5976). Found (%): C, 48.34; H, 3.10. C7H5Cl2N.
Found (%): C, 48.31; H, 2.90. IR, ν/cm1: 1620, 1590, 830.
1H NMR, δ: 6.84 (s, 1 H, CH=); 7.33 (dd, 1 H, Py, J = 8.1
and 4.3 Hz); 7.97 (br.d, 1 H, Py, J = 8.1 Hz); 8.55 (d, 1 H,
C(6)H, J = 4.3 Hz); 8.68 (s, 1 H, C(2)H). 13C NMR, δ: 123.2
(CH=); 125.2 (Py); 129.0 (=CCl2); 130.8 (Py); 134.9 (Py);
149.1 (Py); 149.8 (Py).
4-(2,2-Dichlorovinyl)pyridine (1x): a very unstable color-
less oil, which rapidly blackened in air. 1H NMR, δ: 6.79 (s,
1 H, CH=); 7.41 (d, 2 H, Py, J = 5.9 Hz); 8.62 (d, 2 H, Py,
J = 5.9 Hz). 13C NMR, δ: 122.5 (Py); 126.2 (CH=); 128.6
(=CCl2); 140.4 (Py); 150.0 (Py).
2-(2,2-Dichlorovinyl)thiophene (1y): m.p. 3536 °C.
Found (%): C, 40.40; H, 2.33. C6H4Cl2S. Found (%): C, 40.24;
H, 2.25. IR, ν/cm1: 1610, 850. 1H NMR, δ: 7.007.04 (m,
1 H, Het); 7.02 (s, 1 H, CH=); 7.17 (br.d, 1 H, Het,
J = 3.7 Hz); 7.36 (br.d, 1 H, Het, J = 5.1 Hz). 13C NMR,
δ: 118.6 (=CCl2); 122.8 (CH=); 126.6 (Het); 127.2 (Het);
17. L. A. Dakin, S. E. Schaus, E. N. Jacobsen, and J. S. Panek,
Tetrahedron Lett., 1998, 39, 8947.
18. V. Gettwert, F. Krebs, and G. Maas, Eur. J. Org. Chem.,
1999, 5, 1213.
19. V. K. Aggarwal, H. Abdel-Rahman, R. V. H. Jones, H. Y.
Lee, and B. D. Reid, J. Am. Chem. Soc., 1994, 116, 5973.
20. V. K. Aggarwal, H. Abdel-Rahman, R. V. H. Jones, and
M. C. H. Standen, Tetrahedron Lett., 1995, 36, 1731.
21. V. K. Aggarwal, J. G. Ford, R. V. H. Jones, and
R. Fieldhouse, Tetrahedron Asymmetry, 1998, 9, 1801.
22. D. Bourissou, O. Guerret, F. P. Gabbai, and G. Bertrand,
Chem. Rev., 2000, 100, 39.
23. M. Assher and D. Vofsi, J. Chem. Soc., (B), 1968, 947.
24. H. Reimlinger, Chem. Ber., 1964, 97, 339.
25. R. L. Hinman, J. Org. Chem., 1960, 25, 1775.
26. C. Broquet-Borgel, Ann. Chimie (Paris), 1958, 204.
27. F. Sauter, P. Stanetty, J. Schulner, W. Sittenthaler, and
U. Jordis, Monatsh. Chem., 1991, 122, 863.
129.3 (Het); 136.2 (Het).
17
3-(2,2-Dichlorovinyl)thiophene (1z): nD
1.5795.
Found (%): C, 40.18; H, 2.37. C6H4Cl2S. Found (%): C, 40.24;
H, 2.25. IR, ν/cm1: 1620, 1580, 840. 1H NMR, δ: 6.82 (s,
1 H, CH=); 7.257.31 (m, 2 H, Het); 7.54 (m, 1 H, Het).
13C NMR, δ: 119.6 (=CCl2); 122.8 (CH=); 125.0 (Het);
127.3 (Het); 133.8 (Het).
This work was financially supported by the Russian
Foundation for Basic Research (Project No. 00-03-
32760a).
Received November 17, 2000;
in revised form February 9, 2001