Abstract
THERE has been considerable interest recently in the problem of C—C bond alternation in polyenes1–5. The preparation by Chapman, Paddock, Paine, Searle and Smith6 of a series of cyclic phosphazenes (PNF2)n, where n = 3, 4 ... 17, raises the same question for heterocyclic systems (AB)n containing π-electrons. On the basis of simple molecular orbital theory, it has been shown for cyclic polyenes that, as the number of atoms in the ring N tends to infinity, the stable configuration has C—C bonds unequal in length2. The critical value of N for which the bonds first become unequal is uncertain; but there is evidence for bond alternation3 in C18H18, C24H24 and C30H30.
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References
Ooshika, Y., J. Phys. Soc. Japan, 12, 1246 (1957).
Longuet-Higgins, H. C., and Salem, L., Proc. Roy. Soc., A, 251, 172 (1959).
Longuet-Higgins, H. C., and Salem, L., Proc. Roy. Soc., A, 257, 445 (1960).
Salem, L., Proc. Camb. Phil. Soc., 57, 353 (1961).
Coulson, C. A., Tetrahedron, 12, 193 (1961).
Chapman, A. C., Paddock, N. L., Paine, D. H., Searle, H. T., and Smith, D. R., J. Chem. Soc., 3608 (1960).
Craig, D. P., and Paddock, N. L., Nature, 181, 1052 (1958).
Dewar, M. J. S., Lucken, E. A. C., and Whitehead, M. A., J. Chem. Soc., 2423 (1960).
Craig, D. P., Heffernan, M. L., Mason, R., and Paddock, N. L., J. Chem. Soc., 1376 (1961).
Craig, D. P., J. Chem. Soc., 997 (1959).
Chapman, A. C., and Paddock, N. L., J. Chem. Soc., 635 (1962).
Dougill, M. W., J. Chem. Soc., 5471 (1961).
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DAVIES, D. Bond-Length Alternation in Heterocyclic Ring Systems. Nature 194, 82–83 (1962). https://doi.org/10.1038/194082a0
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DOI: https://doi.org/10.1038/194082a0
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