Abstract
Photolysis of 3-ferrocenyl-3-methyl- and 3-ferrocenyl-3-isopropylcyclopropenes was studied. Sensitized irradiation (triplet excitation) afforded [2+2]-cycloaddition products, viz., tricyclohexane derivatives. Direct irradiation (singlet excitation) of methyl-substituted ferrocenylcyclopropene gave rise to 2-ferrocenylbut-1-en-3-yne and trans-2-ferrocenylbut-2-ene. The isopropyl analog was converted into 1-ferrocenyl-4,4-dimethylcyclobutene. The reaction of this cyclopropene with 2-ferrocenyl-3-methylbut-1-ene afforded 1,3-diferrocenyl-3-isopropyl-6,6-dimethylcyclohexene. The latter compound and 3,6-diferrocenyl-3,6-diisopropyltricyclo[3.1.0.02,4]hexane were studied by X-ray diffraction analysis. Possible reaction pathways are discussed.
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References
A. Padwa, J. Am. Chem. Soc., 1979, 101, 310.
D. R. Arnold, J. A. Pincock, and R. Morchat, J. Am. Chem. Soc., 1973, 95, 7536.
J. A. Pincock and A. Moutsokapas, Can. J. Chem., 1977, 55, 979.
H. E. Zimmerman and S. M. Aasen, J. Am. Chem. Soc., 1977, 99, 2342.
H. E. Zimmerman and S. M. Aasen, J. Org. Chem., 1978, 43, 1493.
S. S. Hixson, P. S. Mariano, and H. E. Zimmerman, Chem. Rev., 1973, 73, 531.
H. E. Zimmerman, R. J. Boettcher, N. E. Buehler, G. E. Keck, and M. G. Steinmetz, J. Am. Chem. Soc., 1976, 98, 7680.
E. I. Klimova, L. Ruiz Ramirez, R. Moreno Esparza, T. Klimova Berestneva, M. Martinez Garcia, N. N. Meleshonkova, and A. V. Churakov, J. Organomet. Chem., 1998, 559, 1.
E. I. Klimova, M. Martinez Garcia, T. Klimova, C. A. Toledano, R. A. Toscano, and L. Ruiz Ramirez, J. Organomet. Chem., 2000, 598, 254.
E. I. Klimova, T. Klimova Berestneva, L. Ruiz Ramirez, M. Martinez Garcia, C. A. Toledano, P. G. Espinosa, and R. A. Toscano, J. Organomet. Chem., 1997, 545–546, 191.
E. I. Klimova, M. Martinez Garcia, T. Klimova, C. A. Toledano, R. A. Toscano, R. Moreno Esparza, and L. Ruiz Ramirez, J. Organomet. Chem., 1998, 566, 175.
A. N. Nesmeyanov, V. A. Sazonova, and V. I. Romancnko, Dokl. Akad. Nauk SSSR, 1964, 155, 1130 [Dokl. Chem., 1964 (Engl. Transl.)].
A. N. Nesmeyanov, V. A. Sazonova, V. I. Romanenko, and G. P. Zol'nikova, Izv. Akad. Nauk SSSR, Ser. Khim., 1965, 1694 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1965, 14 (Engl. Transl.)].
A. N. Nesmeyanov, V. A. Sazonova, A. V. Gerasimenko, and N. S. Sazonova, Dokl. Akad. Nauk SSSR, 1963, 149, 1354 [Dokl. Chem., 1963 (Engl. Transl.)].
G. L. Closs, Adv. Alicyclic Chem., 1966, 1, 53.
V. V. Plemenkov, Kh. Z. Giniyatov, Ya. Ya. Villem, N. V. Villem, L. S. Surmina, and I. G. Bolesov, Dokl. Akad. Nauk SSSR, 1980, 254, 895 [Dokl. Chem., 1980 (Engl. Transl.)].
D. F. Eaton, R. G. Bergman, and G. S. Hammond, J. Am. Chem. Soc., 1972, 94, 1351.
R. E. Long, H. Maddox, and K. N. Trueblood, Acta Crystallogr., Sect. B, 1969, 25, 2083.
A. Hartman and F. L. Hirschfeld, Acta Crystallogr., Sect. B, 1964, 20, 80.
A. A. Almenningen, O. Bastiansen, and P. N. Scanche, Acta Chem. Scand., 1961, 15, 711.
E. Benedetti, P. Corradini, and C. Pedone, Acta Crystallogr., Sect. B, 1970, 26, 493.
E. Adman and T. N. Margulis, J. Phys. Chem., 1969, 73, 1480.
K. Gollnick and G. O. Schenck, Pure Appl. Chem., 1964, 9, 507.
E. I. Klimova, M. Martinez Garcia, T. Klimova, L. Ruiz Ramirez, and J. M. Mendez Stevalet, Mendeleev Commun., 1999, 234.
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Klimova, T., Klimova, E.I., Martinez Garcia, M. et al. Photochemical transformations of 3-alkyl-3-ferrocenylcyclopropenes. Russian Chemical Bulletin 49, 2059–2064 (2000). https://doi.org/10.1023/A:1009588312440
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DOI: https://doi.org/10.1023/A:1009588312440