Ferrocenyl and pyridyl methylenepyrans as potential precursors of organometallic electron-rich extended bipyrans: Synthesis, characterization and crystal structure

Journal of Organometallic Chemistry

Volumn 695, Issue 2, 2010, Pages 235-243

  Ba, Fatou ^a   Robin Le Guen, Francoise ^a   Cabon, Nolwenn ^a   Le Poul, Pascal ^a   Golhen, Stéphane ^b   Le Poul, Nicolas ^c   Caro, Bertrand ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

Author keywords

Electron rich molecules; Ferrocenyl methylenepyrans; Formylation; Pyridyl methylenepyrans

Indexed keywords

ALDEHYDES; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS;

13C NMR SPECTROSCOPY; ELECTRON-RICH; FERROCENYL; FORMYLATION; MASS SPECTROSCOPY; PYRIDYL; REPRESENTATIVE COMPOUND; WITTIG REACTION;

CRYSTAL STRUCTURE;

EID: 72749109627     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.10.006     Document Type: Article

References (112)

1. Meyers F., Bredas J.L., and Zyss J. J. Am. Chem. Soc. 114 (1992) 2914-2921
2. Jen A.K.-Y., Pushkara Rao V., Drost K.J., Wong K.-Y., and Cava M.P. J. Chem. Soc., Chem. Commun. (1994) 2057-2058
3. Andreu R., Garin J., Orduna J., Alcala R., and Villacampa B. Org. Lett. 5 17 (2003) 3143-3146
4. Gorgues A., Hudhomme P., and Salle M. Chem. Rev. 104 (2004) 5151-5184
5. Naka K., Gelover-Santiago A., and Chujo Y. J. Polym. Sci., Part A: Polym. Chem. 42 (2004) 5872-5876
6. Robin-Le Guen F., Le Poul P., and Caro B. Tetrahedron Lett. 45 (2004) 7843-7846
7. Dolder S., Liu S.-X., Guegano X., Atanasov M., Daul C.A., Leiggener C., Hauser A., Neels A., and Decurtins S. Tetrahedron 62 (2006) 11106-11111
8. Granados A.M., Fracaroli A.M., De Rossi R.H., Fuertes P., and Torroba T. Chem. Commun. (2008) 483-485
9. Batail P. Chem. Rev. (2004) 4887-4890 (Special issue)
10. Fourmigue M., Johansen I., Boubekeur K., Nelson C., and Batail P. J. Am. Chem. Soc. 115 (1993) 3752-3759
11. Clausen R.P., and Becher J. Tetrahedron 52 9 (1996) 3171-3188
12. Lorcy D., Carlier R., Robert A., Tallec A., Le Magueres P., and Ouahab L. J. Org. Chem. 60 (1995) 2443-2447
13. Hapiot P., Lorcy D., Tallec A., Carlier R., and Robert A. J. Phys. Chem. 100 (1996) 14823-14827
14. Lorcy D., Le Magueres P., Rimbaud C., Ouahab L., Delhaes P., Carlier R., Tallec A., and Robert A. Synth. Met. 86 (1997) 1831-1832
15. Lorcy D., Guerin D., Boubekeur K., Carlier R., Hascoet P., Tallec A., and Robert A. J. Chem. Soc., Perkin Trans. 1 (2000) 2719-2723
16. Imakubo T., Iijima T., Kobayashi K., and Kato R. Synth. Met. 120 (2001) 899-900
17. Carlier R., Hapiot P., Lorcy D., Robert A., and Tallec A. Electrochim. Acta 46 (2001) 3269-3277
18. Leriche P., Roquet S., Pillerel N., Mabon G., and Frere P. Tetrahedron Lett. 44 (2003) 1623-1626
19. Guerro M., Carlier R., Boubekeur K., Lorcy D., and Hapiot P. J. Am. Chem. Soc. 125 (2003) 3159-3167
20. Tetrahedron Lett. 45 (2004) 2535-2539
21. Osada M., Kumagai T., Sigumoto M., Nishida J., and Yamashita Y. Synth. Met. 152 (2005) 429-432
22. Frere P., and Skabara P. Chem. Soc. Rev. 34 (2005) 69-98
23. Guerro M., and Lorcy D. Tetrahedron Lett. 46 (2005) 5499-5502
24. Navarro A.-E., Moggia F., Moustrou C., Heynderickx A., Fages F., Leriche P., and Brisset H. Tetrahedron 61 (2005) 423-428
25. Sarhan A.A.O. Tetrahedron 61 (2005) 3889-3932
26. Reynolds G.A., and Van Allan J.A. J. Org. Chem. 34 9 (1968) 2736-2741
27. Chen C.H., and Reynolds G.G.A. J. Org. Chem. 45 (1980) 2449-2453
28. Reynolds G.A., and Chen C.H. J. Heterocyclic Chem. 18 (1981) 627-629
29. Reynolds G.A., and Chen C.H. J. Org. Chem. 46 (1981) 184-185
30. Chen C.H., Doney J.J., and Reynolds G.A. J. Org. Chem. 47 (1982) 680-684
31. Detty M.R., and Murray B.J. J. Org. Chem. 47 27 (1982) 5235-5239
32. Balaban A.T., Fahmy M., Gheorghiu M.D., and Wray V. Liebigs Ann. Chem. (1983) 1807-1817
33. Doney J.J., and Chen C.H. Synthesis (1983) 491-492
34. Saeva F.D., Doney J.J., and Morgan B.P. J. Org. Chem. 49 (1984) 2027-2028
35. Balaban A.T. Liebigs Ann. Chem. (1985) 1587-1595
36. Chen C.H., Doney J.J., Reynolds G.A., and Saeva F.D. J. Org. Chem. 48 (1982) 2757-2761
37. Katritzky A.R., Czerney P., and Levell J.R. J. Org. Chem. 62 (1987) 8198-8200
38. Alizon J., Gallice J., Robert H., Delplanque G., Weyl C., Fabre C., and Strzelecka H. Mol. Cryst. Liq. Cryst. 33 (1976) 91-100
39. Alizon J., Gallice J., Robert H., Delplanque G., Weyl C., Fabre C., and Strzelecka H. Mol. Cryst. Liq. Cryst. 32 (1976) 157-159
40. Fabre C., Fugnitto R., and Stzrelecka H. C.R. Acad. Sci. Paris (1976) 175-177
41. Sandman B.J., Fisher A.P., Holmes T.J., and Epstein A. J. Chem. Soc., Chem. Commun. (1997) 687-688
42. Sandman D.J., Holmes T.J., and Warner D.E. J. Org. Chem. 44 5 (1979) 880-881
43. Detty M.R., Murray B.J., and Perlstein J. Tetrahedron Lett. 24 (1983) 539-542
44. Albouy P.A., Pouget J.P., and Strzelecka H. Phys. Rev. 35 (1987) 173-188
45. Sandman D.J., Epstein A.J., Holmes T.J., and Fisher A.P. J. Chem. Soc., Chem. Commun. (1977) 177-178
46. Nakasuji K.N., Takatoh K., Nakatsuka M., and Murata I. J. Chem. Soc., Chem. Commun. (1981) 717-718
47. Nakasuji N., Nakatsuka M., and Murata I. J. Chem. Soc., Chem. Commun. (1981) 1143-1145
48. Detty M.R., Hasset J.W., Murray B.J., and Reynolds G.A. Tetrahedron 41 21 (1985) 4853-4859
49. Shiomi Y., Aso Y., Otsubo T., and Ogura F. J. Chem. Soc., Chem. Commun. (1988) 822-823
50. Sandman D.J., Ceasar G.P., Fisher A.P., Schramm E., Titus D.D., and Baker A.D. Chem. Mater. 1 (1989) 421-427
51. Yui K., Aso Y., Otsubo T., and Ogura F. Bull. Chem. Soc. Jpn. 62 (1989) 1539-1546
52. Yui K., Ishida H., Aso Y., Otsubo T., Ogura F., Kawamoto A., and Tanaka J. Bull. Chem. Soc. Jpn. 62 (1989) 1547-1555
53. Strzelecka H., Vicente R., Ribas J., Legros J.-P., Cassoux P., Petit P., and Andre J.-J. Polyhedron 10 7 (1991) 687-695
54. Ishida H., Yui K., Aso Y., Otsubo T., and Ogura F. Bull. Chem. Soc. Jpn. 63 (1990) 2828-2835
55. Misaki Y., Fujiwara H., Maruyama T., and Yamabe T. Synth. Met. 70 (1995) 1147-1148
56. Misaki Y., Fujiwara H., and Yamabe T. J. Org. Chem. 61 (1996) 3650-3656
57. Kaibuki T., Misaki Y., Takimiya K., Morikami A., and Otsubo T. Synth. Met. 102 (1999) 1621-1622
58. Misaki Y., Fujiwara H., Maruyama T., Taniguchi M., Yamabe T., Mori T., Mori H., and Tanaka S. Chem. Mater. 11 (1999) 2360-2368
59. Takahashi K., Nakayashi T., Misaki Y., and Tanaka J. Mol. Cryst. Liq. Cryst. 376 (2002) 107-112
60. Detty M.R., and Gibson S.L. Organometallics 11 (1992) 2147-2156
61. Detty M.R., and Merkel P.B. J. Am. Chem. Soc. 112 (1990) 3845-3855
62. Fugnitto R., Strzelecka H., Zann A., Dubois J.-C., and Billard J. J. Chem. Soc., Chem. Commun. (1980) 271-272
63. Savea F.D., Reynolds G.A., and Kaszcuk L. Angew. J. Am. Chem. Soc. 104 (1982) 3524-3525
64. Beckmann S., Etzbach K.-H., Kramer P., Lukaszuk K., Matschiner R., Schmidt A.J., Schumacher P., Sens R., Seybold G., Wortmann R., and Wurthner F. Adv. Mater. 11 7 (1999) 536-541
65. Yongjun L., Ying L., Xian Z., and Chengbu L. Int. J. Quant. Chem. 82 (2001) 65-72
66. Koeckelberghs G., De Groof L., Perez-Moreno J., Asselberghs I., Clays K., Verbiest T., and Samyn C. Tetrahedron 64 (2008) 3772-3781
67. Feringa B.L. J. Org. Chem. 72 (2007) 6635-6652
68. Senechal-Tocquer M.-C., Salmain M., Maliszca K.L., Top S., Jaouen G., Senechal D., and Caro B. Bioconjugate Chem. 5 (1994) 655-659
69. Maliska K.L., Top S., Vaisserman J., Caro B., Sénéchal-Tocquer M.-C., Sénéchal D., Triki S., Kahlal S., Butten F., Mc Glinchey J.P., and Jaouen G. Organometallics 14 (1995) 5273-5280
70. Caro B., Robin-Le Guen F., Salmain M., and Jaouen G. Tetrahedron 56 (2000) 257
71. Engan D., Salmain M., Mc Ardel P., Jaouen G., and Caro B. Spectrochim. Acta 56 (2002) 941-951
72. Salmain M., Caro B., Robin-Le Guen F., Blais J.-C., and Jaouen G. Chem. Biochem. 5 (2004) 99-109
73. Caro B., Le Poul P., Robin-Le Guen F., Sénéchal-Tocquer M.-C., and Vaisserman J. Tetrahedron Lett. 39 (1998) 557-560
74. Caro B., Le Poul P., Robin-Le Guen F., Sénéchal-Tocquer M.-C., Saillard J.-Y., Kahlal S., Ouahab L., and Golhen S. Eur. J. Org. Chem. (2000) 577-581
75. Caro B., Le Poul P., Robin-Le Guen F., Saillard J.-Y., Kahlal S., Moinet C., Le Poul N., and Vaissermann J. Tetrahedron 58 (2002) 7519-7530
76. Le Bihan J.-Y., Faux N., Caro B., Robin-Le Guen F., and Le Poul P. J. Organomet. Chem. 692 (2007) 5517-5522
77. Robin-Le Guen F., Le Poul P., Caro B., Pichon R., and Kervarec N. J. Organomet. Chem. 626 (2001) 37-42
78. Faux N., Caro B., Robin-Le Guen F., Le Poul P., Nakatani K., and Ishow E. J. Organomet. Chem. 690 (2005) 4982-4988
79. Milan L., Fuentealba M., Manzur C., Carillo D., Faux N., Caro B., Robin-Le Guen F., Sinbandhit S., Ledoux-Rak I., and Hamon J.R. Eur. J. Inorg. Chem. (2006) 1131-1138
80. Robin-Le Guen F., Le Poul P., Caro B., Faux N., Le Poul N., and Greeen J. Tetrahedron Lett. 43 (2002) 3967-3970
81. Faux N., Robin-Le Guen F., Le Poul P., Caro B., Le Poul N., Le Mest Y., Green S.J., Le Roux S., Kahlal S., and Saillard J.-Y. Tetrahedron 63 (2007) 7142-7153
82. Ba F., Cabon N., Robin-Le Guen F., Le Poul P., Le Poul N., Le Mest Y., Golhen S., and Caro B. Organometallics 27 (2008) 6396-6399
83. Zhdanov Y.A., Kriven S.V., and Polenov V.A. Khim. Geterotsikl. Soeden. (1969) 368
84. Reynolds G.A., and Chen C.H. J. Org. Chem. 45 (1980) 2453-2458
85. Abaev V.T., Kisarova L.I., Emanuilidi S.E., Bumber A.A., Mikhailov I.-E., Blank I.B., Yanovskii A.I., Struchkov Y.T., and Okhlobystin O.Y. Z. Obshchei Khim. 59 7 (1989) 1506-1515
86. Mueller-Westerhoff U.T., Yang Z., and Ingram G.J. J. Organomet. Chem. 463 (1993) 163-167
87. Chiffre J., Averseng F., Balavoine G.G.A., Daran J.-C., Iftime G., Lacroix P.G., Manoury E., and Nakatani N. Eur. J. Inorg. Chem. (2001) 2221-2226
88. Lopez-Alberca M.P., Mancheno M.J., Fernandez J., Gomez-Callego I., Sierra M., and Torres M.A. Org. Lett. 9 (2007) 1757-1759
89. Barluenga J., Barrio P., Vicente R., Lopez L.A., and Tomas M. J. Org. Chem. 689 (2004) 3793-3799
90. Del Amo J.C., Mancheno M.J., Gomez-Gallego M., and Sierra M.A. Organometallics 23 (2004) 5015-5022
91. Sierra M.A., Del Amo J.C., Mancheno M.J., Gomez-Callego M., and Torres M.R. Chem. Comm. (2002) 1842-1843
92. Sierra M.A., Del Amo J.C., Mancheno M.J., and Gomez-Callego M. J. Am. Chem. Soc. 123 (2001) 851-861
93. Sierra M.A., Mancheno M.J., Saez E., and Del Amo J.C. J. Am. Chem. Soc. 120 (1998) 6812-6813
94. Fernandez I., Mancheno M.J., Vicente R., Lopez L.A., and Sierra M.A. Chem. Eur. J. 14 (2008) 11222-11230
95. Fourmigue M., and Batail P. Chem. Rev. 104 (2004) 5379-5418
96. Nicholas K.M. Acc. Chem. Res. 20 (1987) 206-214
97. Caro B., Robin-Le Guen F., Sénéchal-Tocquer M.-C., Prat V., and Vaissermann J. J. Organomet. Chem. 543 (1997) 87-92
98. Caro B., Sénéchal-Tocquer M.-C., Robin-Le Guen F., and Le Poul P. J. Organomet. Chem. 585 (1999) 43-52
99. Mata J.A., and Peris E. J. Chem. Soc., Dalton Trans. (2001) 3634-3640
100. Gholami M., and Tykwinski R. Chem. Rev. 106 (2006) 4997-5027
101. Bryce M.R., Coffin M.A., Skabara P.J., Moore J.M., Batsanov A.S., and Howard J.A.K. Chem. Eur. J. 6 (2000) 1955-1962
102. Le Stang S., Lenz D., Paul F., and Lapinte C. J. Organomet. Chem 572 (1999) 189-192
103. Le Bozec H., and Renouard T. Eur. J. Inorg. Chem. (2000) 229-239
104. Hameed A., Rybarczyk-Pirek A., and Zakrzewski J. J. Organomet. Chem. 656 (2002) 102-107
105. Doney J.J., Chen C.H., and Luss H.R. Tetrahedron Lett. 23 (1982) 1747-1750
106. Krivan S.V., Voziyanova O.F., and Baranov S.N. Zh. Obshch. Kim. 42 (1972) 298
107. Krivan S.V., Voziyanova O.F., and Baranov S.N. Chem. Abstr. 77 (1972) 34224
108. For the ferrocenyl pyran compound 1, DFT calculations have shown that the HOMO is mainly localized on the iron atom. S. Kahlal (Sciences Chimiques de Rennes, UMR CNRS 6226), unpublished results.
109. Due to the presence of two pyran rings in 2, the diradical cationic species would lead to several dimerized compounds. In addition, polymerization reaction cannot be ruled out. Unfortunately oxidation of compound 2 using ferricinium salt led to an undefined dark solid.
110. Moore A.J., Bryce M.R., Skabara P.J., Batsanov A.S., Goldenberg L.M., and Howard J.A.K. J. Chem. Soc., Perkin Trans. 1 (1997) 3443
111. Doisneau G., Balavoine G., and Filleben-Khan T. J. Organomet. Chem. 425 (1992) 113
112. Skeldrick G.M. shelx-97, Programs for Solution Refinement of Crystal Structures (1997), University of Göttingen, Germany