Electronic Effects on the Reactivity of Cross-Conjugated Carbonyl Systems with Fe2(CO)9
Keywords:
Iron(0) complexes, C-S bond activation, reactivity, Hammett plot, X-ray diffractionAbstract
Abstract. The electronic effects induced by p-substituents on the phenyl ring of several novel crossconjugated carbonyl compounds [4-p-R-phenyl-1-(1,3-dithiolane-2-ylidene)-3E-butene-2-one, where R= NO2, Cl, Br, OMe, NEt2 (2-6),] and their reactivity towards Fe2(CO)9 have been studied using a Hammett plot. The structure of two compounds (3 and 4b) was fully established by X-ray diffraction analysis.
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References
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2. Howell, J.A. S.; Johnson, B.f. G.; Josty, P.L.; Lewis, J.; J. Organomet. Chem. 1972, 39, 329; Domingos, J. P.; Howell, J. S. A.; Johnson, B. F. G.; Lewis, J.; Inorg. Synth. 1976, 16, 103; Fleckner, H.; Grevels, F.W.; Hess, D.; J. Am. Chem. Soc. 1984, 106, 2027; Knölker, H. J.; Baum, G.; Foitzik, N.; Goesmann, H.; Gonser, P.; Jones, P. G.; Röttele, H.; Eur. J. Inorg. Chem. 1998, 993.
3. Brandsna, L.; Vasilesky, S. F.; Verbre, H. D.; Application of Transition Metal Catalyst in Organic Chemistry, Springer: New York, 1999, p.254-307; Barton D. H. R.; Gunatilaka, A. A. L.;
Nakanishi, T.; Patin, H.; Widdowson, D. A.; Worth, B. R.; J. Chem Soc. Perkin Trans.1 1976, 821; Evans, G.; Johnson, B. F.G.; Lewis, J.; J.Organomet. Chem. 1975, 102, 507.
4. Cox, L. R.; Ley, S. V.; Chem Soc. Rev. 1998, 27, 301; Takemoto, Y.; Baba, Y.; Yoshikawa, N.; Iwata, C.; Tanaka, T.; Ibuka, T.; Chem. Commun. 1998, 1911; Knölker, H. J.; Chem. Soc. Rev.
1999, 28, 151; Frank-Neuman, M.; Olson, P. J.; Synlett 1991, 891; Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W.; Tetrahedron Lett. 1994, 32, 5892; Prahald, V.; Donaldson, W. A.; Tetrahedron Lett. 1996, 37, 9169; Benvegnu, T. J.; Toupet, L. J.; Grée, R.; Tetrahedron 1996, 52, 11811; Benvegnu, T. J.; Grée, R.; Tetrahedron 1996, 52, 11821. Iwata, C.; Takemoto, Y.; Chem. Commun. 1996, 2497.
5. Alvarez, C.; Gutiérrez, R.; Toscano, R. A.; Moya, M.; Velasco, L.; Rosas, R.; Tapia, R.; Penieres, G.; J. Coord. Chem. 1999, 48, 383; Alvarez-Toledano, C.; Gutiérrez-Pérez, R.; Toscano, R. A.; Moya-Cabrera, M.; Haquet, T.; Ortega, M. C.; Cabrera, A.; Polyhedron 2001, 20, 215; Alvarez-Toledano, C.; Enríquez, J.; Toscano, R. A.; Martínez-García, M.; Cortés-Cortés, E.; Osornio, Y.; García, O.; Gutierrez-Pérez, R.; J. Organomet. Chem. 1999, 577, 38; Ortega, C.; Gutiérrez, R.; Sharma, P.; Gómez, E.; Toscano, A.; López, J. G.; Penieres, G.; Alvarez C.; Trends Organomet. Chem. 2002, 4, 19.
6. Ortega-Jiménez, F.; Ortega-Alfaro, M. C.; López-Cortés, J. G.; Gutiérrez-Pérez, R.; Toscano, R. A.; Velasco-Ibarra, L.; Peña-Cabrera, E.; Alvarez-Toledano, C.; Organometallics 2000, 19, 4127.
7. Karl Dieter, R.; Tetrahedron 1986, 42, 3029; Yates, P.; Lynch, T. R.; Moore, D. R.; Can. J. Chem. 1971, 49, 1467.
8. Shriver, D. F.; Whitmire K. H. In Comprehensive Organometallic Chemistry. The Synthesis, Reactions and Structures of Organometallic Compounds; Wilkinson, G.; Stone, F. G.; Abel, E. W., eds.; Pergamon Press: Oxford, 1982,vol. 4, p.251,252.
9. Huges, D. L.; Leigh, G. L.; Paulson, D.; Inorg. Chim. Acta 1986, 120, 191; King, R. B.; J. Am. Chem. Soc. 1963, 85, 1584.
10. Bernès, S.; Toscano, R. A.; Cano, A. C.; Mellado, O. G.; Alvarez-Toledano, C.; Rudler, H.; Daran, J.; J. Organomet. Chem. 1995, 498, 15; Alvarez-Toledano, C.; Hernández-Ortega, S.; Bernès, S.; Gutiérrez-Pérez, R.; García-Mellado, O.; J. Organomet. Chem. 1997, 549, 49.
11. Ortega-Alfaro, M. C.; Hernández, N.; Cerna, I.; López-Cortés, J. G.; Gómez, E.; Toscano, R. A.; Alvarez-Toledano, C.; J. Organomet. Chem. 2004, 689, 885.
12. Howell, J. A. S.; Johnson, B. F.; Josty, P. L.; Lewis, J.; J. Organomet. Chem. 1972, 39, 329.
13. Geribaldi, S.; Azzaro, M.; Spectrochim. Acta 1982, 38A, 779; Ewing, D. F. In Correlation Analysis in Chemistry: Recent Advances; Chapman, N. B.; Shorter, J., eds.; Plenum: NY, 1978.
14. Hansch, C.; Leo, A.; Taft, R. W.; Chem. Rev. 1991, 91, 165.
15. Smith, M. B.; March, J.; Advanced Organic Chemistry. Reactions, Mechanims and Structure. 5th ed., Willey: USA, 2001, p 363-380.
16. Pearson, A.J.; Iron Compounds in Organic Chemistry, Academic Press: CA, 1994, p. 199-270.
17. Reichenbach, G.; Cardaci, G.; Aloisi, G. G.; J. Organomet. Chem. 1977, 134, 47.
18. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Canalli, M.; J. Appl. Cryst. 1994, 27, 435.
19. Sheldrick, G. M.; SHELXL-97 Program for Refinement of Crystal Structures, Univ. of Goettingen, Germany, 1997.
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