Collect. Czech. Chem. Commun.
2004, 69, 351-364
https://doi.org/10.1135/cccc20040351
Reaction of Zirconacyclopentadienes with Ethynylferrocenes
Lenka Dufkováa, Hiroshi Matsumuraa, David Nečasa, Petr Štěpničkab, Filip Uhlíkc and Martin Kotoraa,*
a Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic
b Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic
c Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic
References
1a. Chem. Rev. 1997, 97, 523.
< H.-H.: https://doi.org/10.1021/cr941164z>
1b. Chem. Rev. 1996, 96, 49.
< M., Tam W.: https://doi.org/10.1021/cr950016l>
1c. Grotjahn D. B. in: Comprehensive Organometallic Chemistry II (E. W. Abel, F. G. A. Stone and G. Wilkinson, Eds), Vol. 12, p. 741. Elsevier Science, Oxford 1995.
1d. Schore N. E. in: Comprehensive Organic Synthesis (B. M. Trost and I. Fleming, Eds), Vol. 5, p. 1129. Pergamon Press Ltd., Oxford 1991.
1e. Harrington P. J.: Transition Metals in Total Synthesis, p. 200. John Wiley & Sons, New York 1990.
1f. Chem. Rev. 1988, 88, 1081.
< N. E.: https://doi.org/10.1021/cr00089a006>
1g. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
< K. P. C.: https://doi.org/10.1002/anie.198405393>
1h. Nicolaou K. C., Sorensen E. J.: Classics in Organic Synthesis (Targets, Strategies, Methods). VCH, Weinheim 1996.
1i. J. Chem. Soc., Perkin Trans. 1 1998, 3873.
< C. P.: https://doi.org/10.1039/a803583k>
1j. Chem. Rev. 2000, 100, 2901.
< S., Yamamoto Y.: https://doi.org/10.1021/cr990281x>
2a. J. Am. Chem. Soc. 1989, 111, 3336.
< E., Holmes S. J., Tour J., Miller J. A., Cederbaum F. E., Swanson D. R., Takahashi T.: https://doi.org/10.1021/ja00191a035>
2b. J. Am. Chem. Soc. 1989, 111, 2870.
< S. L., Nielsen R. B.: https://doi.org/10.1021/ja00190a021>
2c. Tetrahedron Lett. 1986, 27, 2829.
< E., Cederbaum F. E., Takahashi T.: https://doi.org/10.1016/S0040-4039(00)84653-5>
3a. J. Chem. Soc., Chem. Commun. 1995, 361.
< T., Xi Z. F., Kotora M.: https://doi.org/10.1039/c39950000361>
3b. J. Am. Chem. Soc. 1998, 120, 1672.
< T., Xi Z. F., Yamazaki A., Liu Y. H., Nakajima K., Kotora M.: https://doi.org/10.1021/ja970869q>
4. J. Am. Chem. Soc. 1999, 121, 11093.
< T., Tsai F. Y., Li Y. Z., Nakajima K., Kotora M.: https://doi.org/10.1021/ja990750c>
5. Heterocycles 2001, 54, 943.
Y. Z., Ura Y., Tsai F. Y., Xu F., Takahashi T.:
6. Chem. Lett. 1999, 1173.
< T., Tsai F. Y., Li Y. Z.: https://doi.org/10.1246/cl.1999.1173>
7. Tetrahedron Lett. 2002, 43, 3313.
< K. T., Chen R. T.: https://doi.org/10.1016/S0040-4039(02)00520-8>
8. J. Am. Chem. Soc. 2003, 125, 4199.
< S. A., Liu F.-Q., Suh M. C., Zürcher S., Haufe M., Mao S. S. H., Tilley T. D.: https://doi.org/10.1021/ja0209161>
9. J. Am. Chem. Soc. 2000, 122, 12876.
< T., Kitamura M., Shen B., Nakajima K.: https://doi.org/10.1021/ja003130g>
10. Tetrahedron Lett. 2002, 43, 3849.
< J. C., Cran J. W., King N. P.: https://doi.org/10.1016/S0040-4039(02)00680-9>
11. Organometallics 1999, 18, 115.
J. C., Cran J. W., McGlinchey M. J.:
12a. Tetrahedron Lett. 1967, 1181.
< K., Soukup H.: https://doi.org/10.1016/S0040-4039(00)90663-4>
12b. Tetrahedron Lett. 1967, 4421.
< M., Brawn N., King B.: https://doi.org/10.1016/S0040-4039(01)89526-5>
12c. Collect. Czech. Chem. Commun. 1997, 62, 1577.
< P., Císařová I., Sedláček J., Vohlídal J., Polášek M.: https://doi.org/10.1135/cccc19971577>
13. Eur. J. Org. Chem. 2003, 2882.
< L., Císařová I., Štěpnička P., Kotora M.: https://doi.org/10.1002/ejoc.200300119>
14. J. Am. Chem. Soc. 1998, 120, 6834.
< J., Verkade J. G.: https://doi.org/10.1021/ja980356z>
15. Z. Naturforsch. A: Phys. Sci. 1979, 34, 1334.
W., Bauer J., Stösser R.:
16. J. Organomet. Chem. 2001, 637–639, 291.
< P., Trojan L., Kubišta J., Ludvík J.: https://doi.org/10.1016/S0022-328X(01)00922-6>
17. J. Am. Chem. Soc. 1975, 97, 1354.
< D., Pople J. A.: https://doi.org/10.1021/ja00839a011>
18a. Jeffrey G. A.: An Introduction to Hydrogen Bonding. Oxford University Press, New York 1997.
18b. Angew. Chem., Int. Ed. 2002, 41, 48.
< T.: https://doi.org/10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U>
18c. J. Chem. Soc., Dalton Trans. 2001, 651.
C. A., Lawson K. R., Perkins J., Urch C. J.:
18d. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
< G. R.: https://doi.org/10.1002/anie.199523111>
19. A list of reference compounds retrieved from the Cambridge structral database [refcode, θ (°)]: 1,8-diferrocenylnaphthalene (CUKKUO, 40.2, 42.2), phenylferrocene (DICBIA, 11.4), (4-nitrophenyl)ferrocene (GEJVUM01, 12.7), 3-[4-(4-methoxyphenoxycarbonyl)phenoxy- carbonyl]propyl 4-ferrocenylbenzoate (GEXQAB, 9.9), (pentaphenylphenyl)ferrocene (HOPQIM, 50.9), 2,2′-diferrocenyl-1,1′-binaphthyl (LEDJIN, 44.2, 6.8), 4-ferrocenyl- phenyl 4-[4′-(methoxycarbonyloxy)phenyl]benzoate (MAYVEN, 2.2), 3′-fluoro-4′- (octyloxy)biphenyl-1-yl 4-ferrocenylbenzoate (MAYVIR, 7.7), 4-(4-ferrocenylphenyl)pyridine (NAGDUU, 10.7), 1,3,5-triferrocenylbenzene (NUDCUK, 13.6, 27.5, 7.3), 4,4-diferro- cenyl-2,2′,3,3′,5,5′,6,6′-octafluorobiphenyl (QANZEK, 32.2, 37.4), 1,2-diferrocenylbenzene (ROQCEF, 68.6, 32.4), 3,5-diferrocenylchlorobenzene (ROQCIJ, 14.7, 12.3), 3,5-diferrocenyl- benzonitrile (ROQCOP, 10.0, 6.8, 14.6, 25.7), 15-ferrocenyl-2,3,5,6,8,9,10,12-octahydro- 1,4,7,10,13-benzopentaoxacyclopentadecine (SIJFOG, 23.3), 2-(ethynylphenyl)ferrocene (SOBQEF, 25.6, 30.2), 1,1-bis(8-ferrocenylnaphthyl)ferrocene (SOKMOU, 45.8, 44.9), 4-ferrocenyl-2′-methyl-4′-nitroazobenzene (TAZYAU, 27.9), 1,5-diferrocenylnaphthalene (TEJXAH, 47.0), 2′-ferrocenyl-2,5′-dimethyl-4-nitroazobenzene (XAQJUU, 36.9, 41.3), 2′,3′-difluoro-4′-octyloxybiphenyl 4-ferrocenylbenzoate (YARHEE, 9.5), 1-[4-(ferro- cenyl)phenyl]-2-(4-pyridyl)ethene (ZETTUN, 11.1, 5.0), 4-ferrocenyl-4′-formylbiphenyl (OFOGUL, 10.8), 1-{4-[(1,4-benzoquinonyl)carbonylamino]phenyl}ferrocene (UFULIQ, 20.2), ethyl 4-ferrocenylbenzoate (LUPSOE, 6.9), isopropyl 4-ferrocenylbenzoate (LUPSUK, 10.5), methyl 4-ferrocenylbenzoate (XUPDAN, 9.4), N-(4-ferrocenylbenzoyl)- L-alanine methyl ester (XUPDER, 4.9), and (4-ferrocenylphenyl) 4-[4-(methoxy- carbonyloxy)phenyl]benzoate (MAYVEN01, 1.4).
20. Org. Synth. 1996, 73, 262.
J., Schottenberger H.:
21. Inorg. Chem. 1966, 5, 1968.
< G. R., Horrocks W. D.: https://doi.org/10.1021/ic50045a029>
22. J. Org. Chem. 1998, 63, 8551.
< S., Krause N.: https://doi.org/10.1021/jo9808021>
23a. Otwinowski Z., Minor W.: HKL Denzo and Scalepack program package. Nonius BV, Delft 1997.
23b. For a reference see: Methods Enzymol. 1997, 276, 307.
< Z., Minor W.: https://doi.org/10.1016/S0076-6879(97)76066-X>
24. J. Appl. Crystallogr. 1994, 27, 435.
A., Burla M. C., Camalli M., Cascarano G., Giacovazzo C., Guagliardi A., Polidori G.:
25. Sheldrick G. M.: SHELXL97. Program for Crystal Structure Refinement from Diffraction Data. University of Göttingen, Göttingen 1997.
26. Spek A. L.: Platon – A Multipurpose Crystallographic Tool (2001); see: http://www.cryst.chem.uu.nl/platon/.
27. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Zakrzewski V. G., Montgomery J. A., Jr., 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., 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.: Gaussian 98, Revision A.9. Gaussian Inc., Pittsburgh 1998.