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Pyrolysis of Esters of Borneol and isoBorneol

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Abstract

IT is generally believed that esters pyrolyse to give the products of cis elimination in a six-membered cyclic transition state1. Recently, however, products corresponding to a trans elimination have been shown to be formed by the pyrolysis of methyl xanthates of some substituted cyclohexanols2. The pyrolyses of xanthates and acetates of 1-alkylcyclohexanols give predominantly the more stable endocyclic olefins3, and both cis and trans elimination have been observed in pyrolyses of chlorosulphites2, and sulphoxides4.

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References

  1. Hurd, C. D., and Bunck, F. H., J. Amer. Chem. Soc., 60, 2419 (1938). O'Connoy, G. L., and Nace, H. R., ibid., 74, 5454 (1952). DePuy, C. H., and King, R. W., Chem. Rev., 60, 431 (1960). Bader, R. F. W., and Bourns, A. N., Canad. J. Chem., 39, 348 (1961).

    Article  CAS  Google Scholar 

  2. Bordwell, F. G., and Landis, P. S., J. Amer. Chem. Soc., 80, 2450 (1958).

    Article  CAS  Google Scholar 

  3. Benseker, R. A., and Hazdra, J. J., J. Amer. Chem. Soc., 81, 228 (1959). Froensdorf, D. E., Collins, C. H., Hammond, G. S., and DePuy, C. H., ibid., 643. Bailey, W. J., and Hale, W. F., ibid., 647 and 651. Bailey, W. J., and Baylouny, R. A., ibid., 2126.

    Article  Google Scholar 

  4. Kingsbury, C. A., and Cram, D. J., J. Amer. Chem. Soc., 82, 1810 (1960).

    Article  CAS  Google Scholar 

  5. Tschugaeff, L. A., J. Russ. Phys. Chem. Soc., 32, 332 (1900).

    Google Scholar 

  6. Hückel, W., Ber., 77, B, 805 (1944).

    Google Scholar 

  7. Dulou, R., and de Botton, M., Bull. Soc. Chim. France, 26, 1337 (1959).

    Google Scholar 

  8. Maccoll, A., Kekulém, 230 (Butterworths, London, 1958). Maccoll, A., and Swinbourne, E. S., Proc. Chem. Soc., 409 (1959).

    Google Scholar 

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BUNTON, C., KHALEELUDDIN, K. & WHITTAKER, D. Pyrolysis of Esters of Borneol and isoBorneol. Nature 190, 715–716 (1961). https://doi.org/10.1038/190715a0

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