Pyrrolo-annelated tetrathiafulvalenes: The parent systems

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5794-5805

  Jeppesen, Jan Oskar ^a   Takimiya, Kazuo ^a,c   Jensen, Frank ^a   Brimert, Thomas ^a   Nielsen, Kent ^a   Thorup, Niels ^b   Becher, Jan ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033832541     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000742a     Document Type: Article

References (59)

1. Ferraris, J. P.; Cowan, D. O.; Walatka, V.; Perlstein, J. H. J. Am. Chem. Soc. 1973, 95, 948-949.
2. (a) Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203-211.
3. (b) Bryce, M. R. J. Mater. Chem. 1995, 5, 1481-1496.
4. (c) Garin, J. Adv. Heterocycl. Chem. 1995, 62, 249-304.
5. (d) Adam, M.; Müllen, K. Adv. Mater. 1994, 6, 439-459.
6. (e) Schukat, G.; Fanghänel, E. Sulfur Rep. 1996, 18, 1-294.
7. Kini, A. M.; Geiser, U.; Wang, H. H.; Carlson, K. D.; Williams, J. M.; Kwok, W. K.; Vandervoort, K. G.; Thompson, J. E.; Stupka, D. L.; Jung, D.; Whangbo, M.-H. Inorg. Chem. 1990, 29, 2555-2557.
8. Lerstrup, K.; Talham, D.; Bloch, A.; Cowan, D. J. Chem. Soc., Chem. Commun. 1982, 336-337.
9. Siquot, Y.; Frère, P.; Nozdryn, T.; Cousseau, J.; Sallé, M.; Jubault, M.; Orduna, J.; Garín, J.; Gorgues, A. Tetrahedron Lett. 1997, 38, 1919-1922.
10. Shu, P.; Chiang, L.; Emge, T.; Holt, D.; Kistenmacher, T.; Lee, M.; Stokes, J.; Poehler, T.; Bloch, A.; Cowan, D. J. Chem. Soc., Chem. Commun. 1981, 920-921.
11. Ketcham, R.; Hörnfeldt, A.-B.; Gronowitch, S. J. Org. Chem. 1984, 49, 1117-1119.
12. (a) Jørgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 23, 41-51.
13. (b) Becher, J.; Li, Z.-T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470.
14. (a) Zong, K.; Chen, W.; Cava, M. P.; Rogers, R. D. J. Org. Chem. 1996, 61, 8117-8124.
15. (b) Chen, W.; Cava, M. P.; Takassi, M. A.; Metzger, R. M. J. Am. Chem. Soc. 1988, 110, 7903-7904.
16. (c) Zong, K.; Cava, M. P. J. Org. Chem. 1997, 62, 1903-1905.
17. The two methyl groups are mandatory in this synthesis because the first step is an electrophilic thiocyanation at the β-positions and they serve to block the more reactive α-positions.
18. (a) Simonsen, K. B.; Zong, K.; Rogers, R. D.; Cava, M. P.; Becher, J. J. Org. Chem. 1997, 62, 679-686.
19. (b) Lau, J.; Nielsen, M. B.; Thorup, N.; Cava, M. P.; Becher, J. Eur. J. Org. Chem. 1999, 3335-3341.
20. For a comprehensive review on pyrrole synthesis, see: Bird, C. W. Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; pp 1-257.
21. A preliminary account on the synthesis of compounds 7 and 23a has recently been published, see: Jeppesen, J. O.; Takimiya, K.; Jensen, F.; Becher, J. Org. Lett. 1999, 1, 1291-1294.
22. (a) Scheffer, J. R.; Ihmels, H. Liebigs Ann./Recl. 1997, 1925-1929.
23. (b) Kim, W.-J.; Kim, B.-J.; Lee, T.-S.; Nam, K.-S.; Kim, K.-J. Heterocycles 1995, 41, 1389-1397.
24. (c) Jendralla, H.; Fisher, G. Ibid. 1995, 41, 1291-1298.
25. (d) Bottino, F.; Grazia, M. D.; Finocchiaro, P.; Fronczek, F. R.; Mamo, A.; Pappalardo, S. J. Org. Chem. 1988, 53, 3521-3529.
26. (e) Stapler, J. T.; Bornstein, J. J. Heterocycl. Chem. 1973, 10, 983-988.
27. The dehydrogenation of N-alkyl/arylsulfonyl-2,5-dihydropyrroles with different oxidation agents has been described, see: (a) Suzuki, T.; Ohyabu, H.; Takayama, H. Heterocycles 1997, 46, 199-202. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464. Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129-138. Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1995, 807-808. (e) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 1100-1102.
28. The dehydrogenation of N-alkyl/arylsulfonyl-2,5-dihydropyrroles with different oxidation agents has been described, see: (a) Suzuki, T.; Ohyabu, H.; Takayama, H. Heterocycles 1997, 46, 199- 202. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464. Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129-138. Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1995, 807-808. (e) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 1100-1102.
29. The dehydrogenation of N-alkyl/arylsulfonyl-2,5-dihydropyrroles with different oxidation agents has been described, see: (a) Suzuki, T.; Ohyabu, H.; Takayama, H. Heterocycles 1997, 46, 199- 202. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464. Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129-138. Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1995, 807-808. (e) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 1100-1102.
30. The dehydrogenation of N-alkyl/arylsulfonyl-2,5-dihydropyrroles with different oxidation agents has been described, see: (a) Suzuki, T.; Ohyabu, H.; Takayama, H. Heterocycles 1997, 46, 199- 202. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464. Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129-138. Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1995, 807-808. (e) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 1100-1102.
31. The dehydrogenation of N-alkyl/arylsulfonyl-2,5-dihydropyrroles with different oxidation agents has been described, see: (a) Suzuki, T.; Ohyabu, H.; Takayama, H. Heterocycles 1997, 46, 199- 202. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464. Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129-138. Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1995, 807-808. (e) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1992, 1100-1102.
32. (a) Svenstrup; N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J. Synthesis 1994, 809-812.
33. (b) Simonsen, K. B.; Svenstrup, N.; Lau, J.; Simonsen, O.; Mørk, P.; Kristensen, G. J.; Becher, J. Synthesis 1995, 407-418.
34. (c) Simonsen, K. B.; Becher, J. Synlett 1997, 1211-1220.
35. Cava, M. P.; Becher, J. Unpublished results.
36. Jeppesen, J. O.; Takimiya, K.; Thorup, N.; Becher, J. Synthesis 1999, 803-810.
37. 3 has been reported by Müllen and co-workers, see: Skabara, P. J.; Müllen, K.; Bryce, M. R.; Howard, J. A. K.; Batsanov, A. S. J. Mater. Chem. 1998, 8, 1719-1724.
38. 3 has been reported in a communication from Gorgues and co-workers, see: Durand, C.; Hudhomme, P.; Duguay, G.; Jubault, M.; Gorgues, A. Chem. Commun. 1998, 361-362.
39. Care must be taken during workup, especially with regard to temperature; otherwise ring opening occurs in the 1,3-dithiole ring and a mixture of 17 and 3,4-bis(methylthio)pyrrole is isolated.
40. Cross-coupling of thione 16a and 2 equiv of 4,5-bis(methylthio)-1,3-dithiol-2-one in neat triethyl phosphite afforded TTF 22a in a considerably lower yield (26%), compared to the cross-coupling reaction between ketone 16b and 4,5-bis(methylthio)-1,3-dithiole-2-thione.
41. Treatment of 22c with 2.1 equiv of cesium hydroxide monohydrate dissolved in MeOH, followed by addition of excess iodomethane, afforded only 22a in 42% yield, together with byproducts where the tosyl group had been partially deprotected and/or the cyanoethyl thiolate protecting groups partially deprotected.
42. At this point it was verified by TLC and PDMS that clean monodeprotection had taken place.
43. Previous results have shown that a primary alcohol functionality is unable to survive the standard trialkyl phosphite coupling, whereas the tert-butyldiphenylsilyl alcohol protecting group is able to withstand the standard coupling conditions, see: (a) Marshallsay, G. J.; Bryce, M. R.; Cooke, G.; Jørgensen, T.; Becher, J.; Reynolds, C. D.; Wood, S. Tetrahedron 1993, 49, 6849-6862. (b) Marshallsay, G. J; Hansen, T. K.; Moore, A. J.; Bryce, M. R.; Becher, J. Synthesis 1995, 926-930.
44. Previous results have shown that a primary alcohol functionality is unable to survive the standard trialkyl phosphite coupling, whereas the tert-butyldiphenylsilyl alcohol protecting group is able to withstand the standard coupling conditions, see: (a) Marshallsay, G. J.; Bryce, M. R.; Cooke, G.; Jørgensen, T.; Becher, J.; Reynolds, C. D.; Wood, S. Tetrahedron 1993, 49, 6849-6862. (b) Marshallsay, G. J; Hansen, T. K.; Moore, A. J.; Bryce, M. R.; Becher, J. Synthesis 1995, 926-930.
45. Passon, M.; Antoine, M.; Chabassier, S.; Geiger, S.; Girard, P.; Richer, D.; Lajudie, P.; Hovath, E.; Leriche, B.; Patte, S. Eur. J. Med. Chem., Chemi Ther. 1974, 9, 591-594.
46. ·+ with the B3LYP/6-31G(d) method and the PCM solvent model, using PM3-optimized geometries.
47. Gaussian 98 (Revision A.5): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Nudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Comperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.
48. Lomholt, C.; Nielsen, M. B.; Becher, J. Unpublished results.
49. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220.
50. (b) Stewart, J. J. P. J. Comput. Chem. 1989, 221-264.
51. Mori, T.; Kobayashi, A.; Sasaki, Y.; Saito, G.; Inokuchi, H. Bull. Chem. Soc. Jpn. 1984, 57, 627-633.
52. The X-ray data and molecular structures for compounds 22b and 24b are included as Supporting Information.
53. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
54. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785.
55. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
56. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys, 1997, 707, 3032.
57. See, for example: Ramondenc, Y.; Schwenninger, R.; Phan, T.; Gruber, K.; Kratky, C.; Kräutler, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 889-891.
58. Steimecke, G.; Sieler, H.-J.; Kirmse, R.; Hoyer, B. Phosphorus Sulfur 1979, 7, 49-55.
59. Hartke, K.; Kissel, T.; Quante, J.; Matusch, R. Chem. Ber. 1980, 113, 1898-1906.