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Stereoisomerism of symm-Dibenzcyclooctadiene and the Salicylides

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Abstract

MOLECULES of the type of symm-dibenzcyclo-octadiene (I) are probably able to exist in two stereoisomeric forms, a rigid trans form (Iα), and a mobile cis form (Iβ) which can assume a variety of configurations. The two would be interconvertible only by breaking and reforming a C—C bond. This novel type of isomerism was first suggested by F. Höhn1 to explain the supposed existence of two disalicylides (II). Such Stereoisomerism was described in some detail by W. Baker, R. Banks, D. R. Lyon and F. G. Mann2 in connexion with the form of (I) prepared by the action of sodium upon o-xylylene dibromide, and this hydrocarbon was shown by X-ray crystallographical methods (Dr. E. Mr Davidson2) to possess the centro-symmetrical trans structure (Iα).

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References

  1. Private communication to Anschütz, R.; see Richter-Anschütz, "Chemie der Kohlenstoffverbindungen", 2, Pt. 2, 393 (12th edit., 1935).

  2. J. Chem. Soc., 27 (1945).

  3. J. Chem. Soc., 891 (1948).

  4. Berichte, 52, 1880 (1919); later references to the disalicylides are ref.5 and Anschütz, R., J. Pract. Chem., 105, 158 (1922); Anschütz, R., and Riepenkröger, K., Annalen, 439, 4(1924); Anschütz, L., and Neher, R., J. Pract. Chem., 159, 264 (1941);, Kohlrausch, K. W. F., J. Pract. Chem., 159, 268 (1941); Anschütz, L., and Mayer, A., J. Pract. Chem., 159, 343 (1942); Kahovec, L., and Kohlrausch, K. W. F., Monatsh., 74, 333 (1943); Anschütz, L., and Neher, R., Berichte, 77, 634 (1944); Anschütz, L., and Gross, G., Berichte, 77, 634 (1944).

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  5. Berichte, 52, 2227 (1919).

  6. Fieser, L. F., and Pechet, M. M., J. Amer. Chem. Soc., 68, 2577 (1946).

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Authors and Affiliations

  1. University, Bristol,

    WILSON BAKER, W. D. OLLIS & T. S. ZEALLEY

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  1. WILSON BAKER
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  2. W. D. OLLIS
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  3. T. S. ZEALLEY
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BAKER, W., OLLIS, W. & ZEALLEY, T. Stereoisomerism of symm-Dibenzcyclooctadiene and the Salicylides. Nature 164, 1049–1050 (1949). https://doi.org/10.1038/1641049a0

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