Conclusions
The iatermolecular orbital theory of interactions has been used to investigate the reaction of singlet CCl2, SiCl2, and GeCl2 with ethylene and 1,3-butadiene and to show that the probability of the synchronous 1,4-cycloaddition of these particles to butadiene increases as we go from dichlorocarbene to dichlorosilylene and dichlorogermylene.
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Literature cited
W. Kirmse, Carbene, Carbenoide und Carben-Analoge, Verlag Chemie, Weinheim (1969); W. Kirmse, Carbene Chemistry, Academic Press, New York (1971); O. M. Nefedov and A. I. Ioffe, Zh. Vses, Khim. O-va im. D. I. Mendeleeva,19, 305 (1974).
O. M. Nefedov and S. P. Kolesnikov, Vysokomoiekul. Soed.,7, 1857 (1965).
W. H. Atwell and D. R. Weyenberg, Usp. Khim.,39, 1244 (1970).
H. Fujimoto and R. Hoffmann, J. Phys. Chem.,78, 1167 (1974).
J. W. Hastie and J. L. Margrave, J. Phys. Chem.,73, 1105 (1969).
L. Salem, J. Amer. Chem. Soc.,90, 543 (1968); Usp. Khim.,38, 1494 (1969).
R. Hoffmann, J. Chem. Phys.,39, 1397 (1963).
E. Clementi and D. L. Raimondi, J. Chem. Phys.,38, 2686 (1963); E. Clementi, D. L. Raimondi, and W. P. Reinhardt, J. Chem. Phys.,47, 1300 (1967).
H. Basch, A. Viste, and H. B. Gray, Theoret. Chim. Acta,3, 458 (1965).
A. K. Mal'tsev, R. G. Mikaélyan, and O. M. Nefedov, Dokl. Akad. Nauk SSSR,201, 901 (1971); Izv. Akad. Nauk SSSR, Ser. Khim., 199 (1971).
G. Mass, R. H. Hauge, and J. L. Margrave, Z. Anorgan. und Allgem. Chem.,392, 295 (1972).
V. I. Kulishov, I. G. Bokii, Yu. T. Struchkov, O. M. Nefedov, S. P. Kolesnikov, and B. L. Perl'mutter, Zh. Strukturn. Khim., 11, 71 (1970).
Handbook of Chemistry [in Russian], Vol. 1, Goskhimizdat (1962).
Yu. A. Kruglyak, G. G. Dyadyusha, V. A. Kuprievich, L. I. Podol'skaya, and G. I. Kagan, Methods for Calculating the Electronic Structure and Spectra of Molecules [in Russian], Naukova Dumka, Kiev (1969).
R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press, New York (1970).
R. Hoffmann, D. M. Hayes, and P. S. Skell, J. Phys. Chem.,76, 664 (1972).
R. Hoffmann, J. Amer. Chem. Soc.,90, 1475 (1968).
N. Bodor, M. J. S. Dewar, and J. S. Wasson, J. Amer. Chem. Soc.,93, 6188 (1971); T. Fueno, S. Nagase, K. Tatsumi, and K. Yamaguchi, Theoret. Chim. Acta,26, 43 (1972); H. Fujimoto, S. Yamabe, and K. Fukui, Bull. Soc. Chem. Japan,45, 2424 (1972); J. W. Mclver, J. Amer. Chem. Soc.,94, 4782 (1972).
D. Seyferth, J.-P. Mui, and R. Damrauer, J. Amer. Chem. Soc.,90, 6182 (1968); I. A, D'yakonov, R. R. Kostikov, and V. S. Aksenov, Reakts. Sposobn. Organ. Soed.,7, 557 (1970); R. R. Kostikov, V. S. Aksenov, and I. A. D'yakonov, Zh. Organ. Khim.,10, 2099 (1974); R. R. Kostikov, A. P. Molchanov, and K. A. Ogloblin, Zh. Organ. Khim.,9, 2541 (1973); R. R. Kostikov, A. P. Molchanov, and A. Ya. Bespalov, Zh. Organ. Khim.,10, 10 (1974); R. N. Shafran, Dissertation, Moscow (1973).
J. Hine, J. Organ. Chem.,31, 1236 (1966); J. Amer. Chem. Soc.,88, 5525 (1966); O. S. Tee and K. Yates, J. Amer. Chem. Soc.,91, 7144 (1969);94, 3074 (1972).
S. P. Kolesnikov, A. I. Ioffe, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 978 (1975).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 343–348, February, 1976.
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Loffe, A.I., Korzhenevich, L.I., Kolesnikov, S.P. et al. On the mechanism of the interaction of dihalocarbenes and their analogs with ethylene and 1,3-butadiene. Russ Chem Bull 25, 323–327 (1976). https://doi.org/10.1007/BF00922467
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DOI: https://doi.org/10.1007/BF00922467