Synthesis and characterization of functionalized ferrocenylsilanes bearing a bulky substituent

Silicon Chemistry

Volumn 3, Issue 3-4, 2007, Pages 199-207

  Sasamori, Takahiro ^a   Kobayashi, Megumi ^a   Nagahora, Noriyoshi ^a   Sugiyama, Yusuke ^a   Tokitoh, Norihiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cyclic voltammetry; Ferrocene; Hydrogen bond; Silicon; Steric protection

Indexed keywords

EID: 33846032684     PISSN: 15690660     EISSN: 15728994     Source Type: Journal    
DOI: 10.1007/s11201-006-9010-y     Document Type: Article

References (19)

1. (a) Sharma, H.K., Vincenti, S.P., Vicari, R., Cervantes, F. & Pannell, K.H. 1990 Organometallics 9, 2109-2116. (b) Dement'ev, V.V., Cervantes-Lee, F., Parkanyi, L., Sharma, H., Pannell, K.H., Nguyen, M.T. & Diaz, A. 1993 Organometallics 12, 1983-1987. (c) Pannell, K.H., Dement'ev, V.V., Li, H., Cervantes-Lee, F., Nguyen, M.T. & Diaz, A.F. 1994 Organometallics 13, 3644-3650. (d) Pannell, K.H., Wang, F., Sharma, H.K. & Cervantes-Lee, F. 2000 Polyhedron 19, 291-295. (e) Sharma, H.K., Pannell, K.H., Ledoux, I., Zyss, J., Ceccanti, A. & Zanello, P. 2000 Organometallics 19, 770-774.
2. (a) Hoh, G.L., Kleinberg, J. & McEwen, W.E. 1961 J. Chem. Soc. 83, 3949-3953. (b) Cerveau, G., Chuit, C., Colomer, E., Corriu, R.J.P. & Reye, C. 1990 Organometallics 9, 2415-2417. (c) Guillaneux, D. & Kagan, H.B. 1995 J. Org. Chem. 60, 2502-2505. (d) Lu, S.X., Strelets, V.V., Ryan, M.F., Pietro, W.J. & Lever, A.B.P. 1996 Inorganic Chemistry 35, 1013-1023. (e) Jain, R., Choi, H., Lalancette, R.A. & Sheridan, J.B. 2005 Organometallics 24, 1468-1476. (f) Jain, R., Lalancette, R.A. & Sheridan, J.B. 2005 Organometallics 24, 1458-1467. (g) Jones, S.C., Barlow, S. & O'Hare, D. 2005 Chem. Eur. J. 11, 4473-4481. (h) Duffy, N.W., Robinson, B.H. & Simpson, J. 1999 J. Organomet. Chem. 573, 36-46.
3. (a) MacLachlan, M.J., Lough, A.J., Geiger, W.E. & Manners, I. 1998 Organometallics 17, 1873-1883. (b) Manners, I. 1998 Can. J. Chem. 76, 371-381. (c) Nguyen, P., Gomez-Elipe, P. & Manners, I. 1999 Chem. Rev. 99, 1515-1548. (d) MacLachlan, M.J., Zheng, J., Thieme, K., Lough, A.J., Manners, I., Mordas, C., LeSuer, R., Geiger, W.E., Liable-Sands, L.M. & Rheingold, A.L. 2000 Polyhedron 19, 275-289. (e) Kulbaba, K. & Manners, I. 2001 Macromol. Rapid Commun. 22, 711-724. (f) Hatanaka, Y., Okada, S., Minami, T., Goto, M. & Shimada, K. 2005 Organometallics 24, 1053-1055. (g) Roerdink, M., Hempenius, M.A. & Vancso, G.J. 2005 Chem. Mater. 17, 1275-1278.
4. (a) MacLachlan, M.J., Zheng, J., Lough, A.J., Manners, I., Mordas, C., LeSuer, R., Geiger, W.E., Liable-Sands, L.M. & Rheingold, A.L. 1999 Organometallics 18, 1337-1345. (b) MacLachlan, M.J., Ginzburg, M., Zheng, J., Knöll, O., Lough, A.J. & Manners, I. 1998 New. J. Chem. 1409-1415. (c) Reyes-Garcia, E.A., Cervantes-Lee, F. & Pannell, K.H. 2001 Organometallics 20, 4734-4740.
5. (a) Suzuki, H., Tokitoh, N. & Okazaki, R. 1994 J. Am. Chem. Soc. 116, 11572-11573. (b) Suzuki, H., Tokitoh, N. & Okazaki, R. 1995 Organometallics 14, 1016-1022. (c) Suzuki, H., Tokitoh, N. & Okazaki, R. 1995 Bull. Chem. Soc. Jpn. 68, 2471-2481. (d) Takeda, N., Suzuki, H., Tokitoh, N. & Okazaki, R. 1997 J. Am. Chem. Soc. 119, 1456-1457. (e) Tokitoh, N., Suzuki, H. & Okazaki, R. 1993 J. Am. Chem. Soc. 115, 10428-10429. (f) Takeda, N., Kajiwara, T. & Tokitoh, N. 2001 Chem. Lett. 30, 1076-1077. (g) Tokitoh, N. & Okazaki, R. 2001 Adv. Organomet. Chem. 47, 121-166. (h) Tokitoh, N. 2004 Acc. Chem. Res. 37, 86-94. (i) Kajiwara, T., Takeda, N., Sasamori, T. & Tokitoh, N. 2004 Organometallics 23, 4723-4734. (j) Kajiwara, T., Takeda, N., Sasamori, T. & Tokitoh, N. 2004 Chem. Commun. 2218-2219. (k) Okazaki, R. & Tokitoh, N. 2000 Acc. Chem. Res. 33, 625-630. (l) Wakita, K., Tokitoh, N., Okazaki, R. & Nagase, S. 2000 Angew. Chem. Int. Ed. 39, 634-635. (m) Takeda, N., Kajiwara, T., Suzuki, H., Okazaki, R. & Tokitoh, N. 2003 Chem. Eur. J. 9, 3530-3543. (n) Tajima, T., Hatano, K., Sasaki, T., Sasamori, T., Takeda, N., Tokitoh, N., Takagi, N. & Nagase, S. 2003 J. Organomet. Chem. 686, 118-126. (o) Shinohara, A., Takeda, N. & Tokitoh, N. 2003 J. Am. Chem. Soc. 125, 10804-10805. (p) Tokitoh, N., Sadahiro, T., Hatano, K., Sasaki, T., Takeda, N. & Okazaki, R. 2002 Chem. Lett. 34-35. (q) Shinohara, A., Takeda, N., Sasamori, T., Matsumoto, T. & Tokitoh, N. 2005 Organometallics 24, 6141-6146. (r) Shinohara, A., Takeda, N., Sasamori, T. & Tokitoh, N. 2005 Bull. Chem. Soc. Jpn. 78, 977-987. (s) Tokitoh, N. 2004 Bull. Chem. Soc. Jpn. 77, 429-441.
6. Blinka, T.A., Helmer, B.J. & West, R. {1984} Adv. Organomet. Chem. 23, {193}-{217}.
7. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 604438 (for 1), 604439 (for 2), and 604440 (for 3). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; E-mail: Depositγcdc.cam.ac.uk.).
8. The reactivity of the newly obtained ferrocenylsilanes, 1-3, will be reported elsewhere.
9. Lickiss, P.D. & Lucas, R. {1996} J. Organomet. Chem. 521, {229}-{234}.
10. Vrček, V. & Bühl, M. {2006} Organometallics 25, {358}-{367}.
11. (a) Trifan, D.S. & Bacskai, R. 1960 J. Am. Chem. Soc. 82, 5010-5011. (b) Baker, A.W. & Bublitz, D.E. 1966 Spectrochim. Acta 22, 1787-1799. (c) Shubina, E.S., Epstein, L.M., Timofeeva, T.V., Struchkov, Y.T., Kreindlin, A.Z., Fadeeva, S.S. & Rybinskaya, M.I. 1988 J. Organomet. Chem. 346, 59-66. (d) Shubina, Y.S. & Epstein, L.M. 1992 J. Mol. Struct. 265, 367-384.
12. Calculated at B3LYP/ 6-31G(d) level. The vibrational frequencies are scaled by 0.96.
13. Deck, P.A., Cheng, X., Stoebenau, E.J., Slebodnick, C., Billodeaux}, D.R. & Fronczek, F.R. {2000} Organometallics 19, {5404}-{5409}.{}
14. Calculated at B3LYP 6-311+G(2d) for Si, 6-31+G(d) for C, H, Br, TZV for Fe. For the basis sets for Fe, see Ahlrichs, R. & May, K. 2000 Phys. Chem. Chem. Phys. 2, 943-945.
15. Pangborn, A.B., Giardello, M.A., Grubbs, R.H., Rosen, R.K. & Timmers, F.J. {1996} Organometallics 15, {1518}-{1520}.
16. Altomare, A., Burla, M., Camalli, M., Cascarano, G., Giacovazzo}, C., Guagliardi, A., Moliterni, A., Polidori, G. & Spagna, R. {1999} J. Appl. Cryst. 32, {115}-{119.}
17. Sheldrick, G.M. {1997} SHELX-97, Program for the Refinement of Crystal Structures. {Germany}: {University of Göttingen}.
18. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., J.A. Montgomery}, J., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, 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., Salvador, P., Dannenberg, J.J., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Baboul, A.G., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S. & Pople, J.A. {2001} Gaussian 98. {Pittsburgh PA}: {Gaussian, Inc.}
19. (a) Becke, A.D. 1988 Phys. Rev. A38, 3098. (b) Becke, A.D. 1993 J. Chem. Phys. 98, 5648. (c) Lee, W.Y. & Parr, R.G. 1988 Phys. Rev. B37, 785.