Abstract
IR studies of SnF2 and hept-1-yne codeposited in an argon matrix at 12 K has revealed new bands at 540, 565, 1011, 2088 and 3256 cm−1, assigned to the formation of a complex between SnF2 and the alkyne. Quantum chemical AM1 and PM3 calculations confirm this assignment to the π-complex of SnF2 and the triple bond of hept-1-yne, and show that the complex forms without an activation barrier. The energy of the formation of the complex according to AM1 and PM3 calculations is 7.4 and 9.1 kcal/mol, respectively. The calculations indicate that the product of the cycloaddition of SnF2 to a triple bond, stannyrene, is significantly less stable than the π-complex.
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References
Nefedov, O. M., Loffe, A.L., and Menchikov L.G., Khimiya Karbenov (Carbene Chemistry), Khimiya, Moscow, 1990 [in Russian], and references cited therein.
A. Krebs and J. Berndt,Tetrahedron Lett., 1983,24, 4083; M. P. Egorov, S. P. Kolesnikov, Yu. T. Struchkov, M. Yu. Antipin, S. V. Sereda, and O. M. Nefedov,J. Organomet. Chem., 1985,290, C27;L. R. Sita and R. D. Bickerstaff,J. Am. Chem. Soc., 1988,110, 5208.
K. N. Houk, N. J. Rondan, and J. Mareda,J. Amer. Chem. Soc., 1984,106, 4291; K. N. Houk, N. J. Rondan, J. Mareda,Tetrahedron, 1985,41, 1555.
P. F. Meier, D. L. Perry, R. H. Hauge, and J. I. Margrave,Inorg. Chem., 1979,18, 2051.
V. I. Faustov, and M. P. Egorov, Abstracts of V-th Conference on the Chemistry of Carbenes, Moscow, 1992, 123 [in Russian]; V. I. Faustov, M. P. Egorov, and O. M. Nefedov,Abstracts of VII-th International conference on the organometallic and coordination chemistry of germanium, tin and lead, 1992, Riga, Latvia, 13.
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart,J. Am. Chem. Soc., 1985,107, 3902.
J. J. P. Stewart,J. Comp. Chem., 1989,10, 221.
M. J. S. Dewar, E. F. Healy, D. R. Kuhn, and A. J. Houlder,Organometallics, 1991,10, 431.
J. J. P. Stewart,J. Comp. Chem., 1991,12, 320.
J. A. Boatz, M. S. Gordon, and L. R. Sita,J. Phys. Chem., 1990,94, 5488.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 54–56, January, 1994.
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Boganov, S.E., Faustov, V.I., Egorov, M.P. et al. Matrix IR spectra and quantum chemical studies of the reaction between difluorostannylene and hept-1-yne. The first direct observation of a carbene analog π-complex with alkne. Russ Chem Bull 43, 47–49 (1994). https://doi.org/10.1007/BF00699133
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DOI: https://doi.org/10.1007/BF00699133