Synthesis of a new polyfluorinated vinylogue of tetrathiafulvalene through 1,3-dipolar cycloaddition of ethyl β-bromoperfluorodithiocrotonate with dimethyl acetylenedicarboxylate

Chemistry - A European Journal

Volumn 9, Issue 18, 2003, Pages 4324-4329

  Timoshenko, Vadim M ^a,b   Bouillon, Jean Philippe ^a   Chernega, Alexander N ^b   Shermolovich, Yuriy G ^a,b   Portella, Charles ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b INSTITUTE OF HYDROBIOLOGY   (Ukraine)

Author keywords

Alkynes; Cycloaddition; Dithiocrotonic acid; Sulfur heterocycles; Tetrathiafulvalene

Indexed keywords

ADDITION REACTIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

CYCLIZATION PRODUCTS;

ORGANIC COMPOUNDS;

1,4 DIFLUORO 2,3 BIS(TRIFLUOROMETHYL)BUT 2 ENE 1,4 DIYLIDENE 2,2' BIS(4',5' DICARBOMETHOXY 1',3' DITHIOLE); 11,14 DIFLUORO 2,3,8,9 TETRAKIS(CARBOMETHOXY) 12,13 BIS(TRIFLUOROMETHYL) 1,4,7,10 TETRATHIADISPIRO[4.0.4.4]TETRADECA 2,8,11,13 TETRAENE; 5,8 DIFLUORO 6,7 BIS(TRIFLUOROMETHYL) 2,3 BIS(CARBOXYMETHYL) 1,4 BENZODITHIINE; ALKYNE; BETA BROMOPERFLUORODITHIOCROTONIC ACID ETHYL ESTER; CROTONIC ACID DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; DIMETHYL ACETYLENEDICARBOXYLATE; HETEROCYCLIC COMPOUND; SULFUR DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; FLUORINATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0141868804     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304839     Document Type: Article

References (45)

1. J.-P. Bouillon, Yu. G. Shermolovich, C. Portella, Tetrahedron Lett. 2001, 42, 2133-2135.
2. P. Gosselin, S. Masson, A. Thuillier, Tetrahedron Lett. 1980, 21, 2421-2424.
3. a) V. N. Drozd, Zh. Org. Khim. 1979, 15, 1106 [Chem. Abstr. 1979, 91, 593229];
4. a) V. N. Drozd, Zh. Org. Khim. 1979, 15, 1106 [Chem. Abstr. 1979, 91, 593229];
5. b) V. N. Drozd, O. A. Popova, Tetrahedron Lett. 1979, 4491-4492;
6. c) V. N. Drozd, O. A. Popova, Zh. Org. Khim. 1980, 16, 2047-2054 [Chem. Abstr. 1981, 94, 139664];
7. c) V. N. Drozd, O. A. Popova, Zh. Org. Khim. 1980, 16, 2047-2054 [Chem. Abstr. 1981, 94, 139664];
8. d) V. N. Drozd, Zh. Org. Khim. 1993, 29, 1089-1094 [Chem. Abstr. 1994, 120, 270188z].
9. d) V. N. Drozd, Zh. Org. Khim. 1993, 29, 1089-1094 [Chem. Abstr. 1994, 120, 270188z].
10. V. M. Timoshenko, J.-P. Bouillon, Yu. G. Shermolovich, C. Portella, Tetrahedron Lett. 2002, 43, 5809-5812.
11. a) M. R. Bryce, Chem. Soc. Rev. 1991, 20, 355-390;
12. b) J. Roncali, J. Mater. Chem. 1997, 7, 2307-2321.
13. a) Z.-I. Yoshida, T. Kawase, H. Awaji, I. Sugimoto, Tetrahedron Lett. 1983, 24, 3469-3472;
14. b) Z.-I. Yoshida, T. Kawase, H. Awaji, S. Yoneda, Tetrahedron Lett. 1983, 24, 3473-3476;
15. c) V. Y. Khodorkovskii, L. N. Veselova, O. Ya. Neiland, Khim. Geterotsikl. Soedin. 1990, 130-135 [Chem. Abstr. 1990, 113, 22868t];
16. c) V. Y. Khodorkovskii, L. N. Veselova, O. Ya. Neiland, Khim. Geterotsikl. Soedin. 1990, 130-135 [Chem. Abstr. 1990, 113, 22868t];
17. d) A. J. Moore, M. R. Bryce, D. J. Ando, M. B. Hursthouse, J. Chem. Soc. Chem. Commun. 1991, 320-321;
18. e) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. M. Metzger, J. Becher, J. Org. Chem. 1991, 56, 2720-2722;
19. f) A. J. Moore, M. R. Bryce, Synthesis 1991, 26-28;
20. g) M. Salle, A. Belyasmine, A. Gorgues, M. Jubault, N. Soyer, Tetrahedron Lett. 1991, 32, 2897-2900;
21. h) P. Frère, A. Belyasmine, Y. Gouriou, M. Jubault, A. Gorgues, G. Duguay, S. Wood, C. D. Reynolds, M. R. Bryce, Bull. Soc. Chim. Fr 1995, 132, 975-984;
22. i) P. Frère, K. Boubekeur, M. Jubault, P. Batail, A. Gorgues, Eur. J. Org. Chem. 2001, 3741-3747;
23. j) P. Frère, M. Allain, E. H. Elandaloussi, E. Levillain, F.-X. Sauvage, A. Riou, J. Roncali, Chem. Eur. J. 2002, 8, 784-792;
24. k) M. B. Nielsen, N. F. Utesch, N. N. P. Moonen, C. Boudon, J.-P. Gisselbrecht, S. Concilio, S. P. Piotto, P. Seiler, P. Günter, M. Gross, F. Diederich, Chem. Eur. J 2002, 8, 3601-3613 and references therein;
25. l) D. Rajagopal, M. V. Lakshmikantham, M. P. Cava, Org. Lett. 2002, 4, 2581-2583;
26. m) P. Leriche, S. Roquet, N. Pillerel, G. Mabon, P. Frère, Tetrahedron Lett. 2003, 44, 1623-1626.
27. H. D. Hartzler, J. Am. Chem. Soc. 1973, 95, 4379-4387.
28. a) R. R. Shumaker, E. M. Engler, J. Am. Chem. Soc. 1980,102, 6651-6652;
29. b) C. Maletzko, W. Sundermeyer, H. Pritzkow, H. Irngartinger, U. Huber-Patz, Chem. Ber. 1991, 124, 2025-2031;
30. c) B. W. Knight, S. T. Purrington, R. D. Bereman, P. Singh, Synthesis 1994, 460-462.
31. Yu. G. Shermolovich, C. Portella, O. Tschen, Bull. Soc. Chim. Fr. 1997, 134, 697-702.
32. a) A. S. Benahmed-Gasmi, P. Frère, A. Belyasmine, K. M. A. Malik, M. B. Hursthouse, A. J. Moore, M. R. Bryce, M. Jubault, A. Gorgues, Tetrahedron Lett. 1993, 34, 2131-2134;
33. b) P. Frère, A. Gorgues, M. Jubault, A. Riou, Y. Gouriou, J. Roncali, Tetrahedron Lett. 1994, 35, 1991-1994.
34. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2, 1987, S1-S19.
35. V.A. Naumov, O. N. Kataeva, Molecular Structure of Organic Compounds of Oxygen and Sulfur, Naurf, Moskow 1990, pp. 113-128 [Chem. Abstr. 1991, 114, 121381f].
36. V.A. Naumov, O. N. Kataeva, Molecular Structure of Organic Compounds of Oxygen and Sulfur, Naurf, Moskow 1990, pp. 113-128 [Chem. Abstr. 1991, 114, 121381f].
37. a) S. C. Cohen, M. L. N. Reddy, A. G. Massey, J. Chem. Soc. Chem. Commun. 1967, 451-453;
38. b) S. C. Cohen, M. L. N. Reddy, A. G. Massey, J. Organomet. Chem. 1968, 11, 563-566;
39. c) S. C. Cohen, A. G. Massey, J. Organomet. Chem. 1968, 12 341-347;
40. d) R. E. Humphries, N. A. A. Al-Jabar, D. Bowen, A. G. Massey, G. B. Deacon, J Organomet. Chem. 1987, 319, 59-67.
41. a) R. D. Chambers, J. A. Cunningham, D. A. Pyke, Tetrahedron 1968, 24, 2783-2787;
42. b) R. D. Chambers, J. A. Cunningham, D. J. Spring, Tetrahedron 1968, 24, 3997-4005.
43. A. C. T. North, D. C. Phillips, F. S. Mathews, Acta Crystallogr. Sect. C 1968, 24, 351-359.
44. J. R. Carruthers, D. J. Watkin, Acta Crystallogr. Sect. C 1979, 35, 698-699.
45. D. J. Watkin, C. K. Prout, J. R. Carruthers, P. W. Betteridge, CRYSTALS, Chemical Crystallography Laboratory, University of Oxford, UK, 1996, Issue 10.