Uncatalyzed reactions of α-(trihaloethylidene)nitroalkanes with push-pull enamines: A new type of ring-ring tautomerism in cyclobutane derivatives and the dramatic effect of the trihalomethyl group on the reaction pathway

Tetrahedron Letters

Volumn 52, Issue 44, 2011, Pages 5764-5768

  Korotaev, Vladislav Yu ^a   Barkov, Alexey Yu ^a   Slepukhin, Pavel A ^b   Kodess, Mikhail I ^b   Sosnovskikh, Vyacheslav Ya ^a  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

1,2 Oxazine N oxides; 1D and 2D NMR spectroscopy; Conjugated nitroalkenes; Cyclobutanes; Michael addition; Push pull enamines; Ring ring tautomerism; X ray diffraction analysis

Indexed keywords

CYCLOBUTANE DERIVATIVE; ENAMINE; NITROALKANE;

ARTICLE; CHEMICAL REACTION; TAUTOMER;

EID: 80054969559     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.109     Document Type: Article

References (40)

1. (a) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001;
2. (b) Yoshikoshi, A.; Miyashita, M. Acc. Chem. Res. 1985, 18, 284.
3. (a) Klenz, O.; Evers, R.; Miethchen, R.; Michalik, M. J. Fluorine Chem. 1997, 81, 205;
4. (b) Tanaka, K.; Mori, T.; Mitsuhashi, K. Bull. Chem. Soc. Jpn. 1993, 66, 263;
5. (c) Tanaka, K.; Mori, T.; Mitsuhashi, K. Chem. Lett. 1989, 1115;
6. (d) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432;
7. (e) Korotaev, V. Y.; Sosnovskikh, V. Y.; Barabanov, M. A.; Barkov, A. Y.; Kodess, M. I. Mendeleev Commun. 2010, 20, 17;
8. (f) Korotaev, V. Y.; Sosnovskikh, V. Y.; Kutyashev, I. B.; Barkov, A. Y.; Matochkina, E. G.; Kodess, M. I. Tetrahedron 2008, 64, 5055;
9. (g) Korotaev, V. Y.; Kutyashev, I. B.; Sosnovskikh, V. Y. Heteroatom Chem. 2005, 16, 492;
10. (h) Turconi, J.; Lebeau, L.; Paris, J.-M.; Mioskowski, C. Tetrahedron Lett. 2006, 47, 121;
11. (i) Korotaev, V. Y.; Barkov, A. Y.; Kodess, M. I.; Kutyashev, I. B.; Slepukhin, P. A.; Zapevalov, A. Y. Izv. Akad. Nauk Ser. Khim. 2009, 1827.
12. (a) Molteni, M.; Consonni, R.; Giovenzana, T.; Malpezzi, L.; Zanda, M. J. Fluorine Chem. 2006, 127, 901;
13. (b) Molteni, M.; Belucci, M. C.; Bigotti, S.; Mazzini, S.; Volonterio, A.; Zanda, M. Org. Biomol. Chem. 2009, 7, 2286.
14. Korotaev, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Sosnovskikh, V. Y. Izv. Akad. Nauk Ser. Khim. 2011, 137.
15. Korotaev, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Kodess, M. I.; Sosnovskikh, V. Y. Mendeleev Commun. 2011, 21, 112.
16. Korotaev, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Kodess, M. I.; Sosnovskikh, V. Y. Mendeleev Commun. 2011, 21, 5.
17. Aizikovich, A. Y.; Korotaev, V. Y.; Kodess, M. I.; Barkov, A. Y. Zh. Org. Khim. 1998, 34, 1149.
18. Russ. J. Org. Chem. (Engl. Transl.) 1998, 34, 1093.
19. (a) Risaliti, A.; Forchiassin, M.; Valentin, E. Tetrahedron 1968, 24, 1889;
20. (b) Felluga, F.; Nitti, P.; Pitacco, G.; Valentin, E. Tetrahedron 1989, 45, 2099;
21. (c) Bradamante, P.; Pitacco, G.; Risaliti, A.; Valentin, E. Tetrahedron Lett. 1982, 23, 2683;
22. (d) Benedetti, F.; Drioli, S.; Nitti, P.; Pitacco, G.; Valentin, E. Arkivoc 2001, v, 140;
23. (e) Felluga, F.; Nitti, P.; Pitacco, G.; Valentin, E. Tetrahedron 1989, 45, 5667;
24. (f) Asaro, F.; Pitacco, G.; Valentin, E. Tetrahedron 1987, 43, 3279;
25. (g) Pitacco, G.; Pizzioli, A.; Valentin, E. Synthesis 1996, 242.
26. (a) Brook, M. A.; Seebach, D. Can. J. Chem. 1987, 65, 836;
27. (b) Seebach, D.; Lyapkalo, I. M.; Dahinden, R. Helv. Chim. Acta 1999, 82, 1829;
28. (c) Ioffe, S. L. In Feuer, H., Ed., second ed.; Nitrile Oxides Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis; John Wiley & Sons: Chichester, 2008; pp 435-748;
29. (d) Smirnov, V. O.; Ioffe, S. L.; Tishkov, A. A.; Khomutova, Y. A.; Nesterov, I. D.; Antipin, M. Y.; Smit, W. A.; Tartakovsky, V. A. J. Org. Chem. 2004, 69, 8485;
30. (e) Klenov, M. S.; Lesiv, A. V.; Khomutova, Y. A.; Nesterov, I. D.; Ioffe, S. L. Synthesis 2004, 1159.
31. (a) Pitacco, G.; Valentin, E. Tetrahedron Lett. 1978, 2339;
32. (b) Nitti, P.; Pitacco, G.; Rinaldi, V.; Valentin, E. Croat. Chem. Acta 1986, 59, 165.
33. (a) Kuehne, M. E.; Foley, L. J. Org. Chem. 1965, 30, 4280;
34. (b) Brannock, K. C.; Bell, A.; Burpitt, R. D.; Kelly, C. A. J. Org. Chem. 1964, 29, 801;
35. (c) Colonna, F. P.; Valentin, E.; Pitacco, G.; Risaliti, A. Tetrahedron 1973, 29, 3011.
36. Korotaev, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Kodess, M. I.; Sosnovskikh, V. Y. Tetrahedron Lett. 2011, 52, 3029.
37. X-ray diffraction study of compounds 7a,c and 8d. Diffraction data were collected at 150 K (7a,c) and 293 K (8d) on an Xcalibur 3 automatic singlecrystal diffractometer (graphite-monochromated MoKa radiation, x-scans). The structures were solved by direct methods and refined by the full-matrix least-squares method using the SHELX-97 program package.14 The H atoms were located geometrically using the riding model. Crystal data for 7a: C14H21F3N2O4, M = 338.33, monoclinic crystals, space group P2(1)/n, a = 9.1640(7), b = 15.0655(10), c = 11.5671(11) Å, a = c = 90.00, b = 92.605(7), V = 1595.3(2) Å3, Z = 4, qcalcd = 1.409 g/cm3, l = 0.125 mm-1, F(000) = 712. Crystal data for 7c: C15H23F3N2O4, M = 352.36, monoclinic crystals, P2(1)/n, a = 6.8672(4), b = 15.2411(10), c = 16.1177(13) Å, a = c = 90.00, b = 90.575(6), V = 1686.9(2) Å3, Z = 4, qcalcd = 1.387 g/cm3, l = 0.121 mm-1, F(0 0 0) = 744. Crystal data for 8d: C14H21F3N2O5, M = 354.33, monoclinic crystals, space group P2(1)/n, a = 8.6234(6), b = 11.4679(9), c = 17.5574(15) Å, a = c = 90.00, b = 102.213(7), V = 1697.0(2), Z = 4, qcalcd = 1.387 g/cm3, l = 0.125 mm-1, F(0 0 0) = 744. Crystallographic data for compounds 7a (CCDC deposition number 831487), 7c (CCDC deposition number 831488) and 8d (CCDC deposition number 831489) have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
38. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.
39. Kostyuk, A. N.; Volochnyuk, D. M.; Sibgatulin, D. A. Synthesis 2008, 161.
40. Kingsbury, C. A.; Sopchik, A. E.; Underwood, G.; Rajan, S. J. Chem. Soc., Perkin Trans. 1982, 2, 867.