Conclusions
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1.
The structures of 20 propellanes, containing all possible combinations of three-, four-, five-, and six-carbon rings were calculated by the MM/2 method. An assessment of their strains was made by means of homodesmotic reactions with partial and complete separation of the rings.
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2.
During fusion of the bicyclic or propellane type along a common bond the most favorable is the combination of a three-membered ring with five- or six-membered rings and also of several five-membered rings, whereas the combination of two small rings or of a six-membered ring with a four-membered ring are unfavorable in energy respects.
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3.
During the construction of the skeleton of the lower propellanes containing more than one strained fragment substantial weakening of the common bond appears at the energy and structural levels, whereas propellanes containing one three- or four-membered ring do not differ in any structural features.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2040–2050, September, 1988.
For previous communication, see [1].
The authors express their gratitude to M. Jones (Princeton University, USA) and P. R. Schleyer (Institute of Organic Chemistry, Erlangen University, Germany) for assistance in the production of the MM/2 program and to L. V. Gurvich (Institute of High Temperatures, Academy of Sciences of the USSR) and J. B. Pedley (Sussex University, Great Britain) for the opportunity to become acquainted with the latest version of the bank of thermochemical values [14] and also to V. I. Faustov for the MINDO/3 program.
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Ioffe, A.I., Svyatkin, V.A. & Nefedov, O.M. Molecular-mechanical analysis of the structure of strained organic molecules. 6. [m.n.k]-Propellanes. Russ Chem Bull 37, 1827–1836 (1988). https://doi.org/10.1007/BF00962498
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DOI: https://doi.org/10.1007/BF00962498