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Optically Active Spirotriterpane in Petroleum Distillates

Nature volume 219, pages 243–246 (1968)Cite this article

Abstract

The structure of a triterpane isolated from a Nigerian crude oil has been determined by X-ray crystallography. The structure could have arisen from a natural triterpene through a molecular rearrangement induced under the conditions of petroleum evolution.

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References

  1. Rosenfeld, W. D., J. Amer. Oil Chemists Soc., 44, 703 (1967).

    Article  CAS  Google Scholar 

  2. Meinsshein, W. G., Bull Amer. Assoc. Petrol. Geol., 43, 925 (1959); Geochim Cosmochim. Acta, 22, 58 (1961).

    Google Scholar 

  3. Marcusson, J., Chem. Z., 32, 377, 391 (1908).

    CAS  Google Scholar 

  4. Louis, M., Rev. Inst. Franc, du Pétrole, 19, 277 (1964); Danieli, N., Gil-Av, E., and Louis, M., Nature (in the press).

    CAS  Google Scholar 

  5. Burlingame, A. L., Haug, P., Belsky, T., and Calvin, M., Proc. US Nut. Acad. Sci., 54, 1406 (1965).

    Article  CAS  ADS  Google Scholar 

  6. McCarthy, E. D., and Calvin, M., Nature, 216, 642 (1967).

    Article  CAS  ADS  Google Scholar 

  7. Studier, M. H., Hayatsu, R., and Anders, E., Geochim. Cosmochim. Acta, 32, 151 (1968).

    Article  CAS  ADS  Google Scholar 

  8. Hills, I. R., Whitehead, E. V., Anders, D. E., Cummins, J. J., and Robinsou, W. E., Chem. Commun., 752 (1966).

  9. Tsuda, Y., Morimoto, A., Sano, T., Inubishi, Y., Mallory, F. B., and Gordon, J. T., Tetrahedron Lett., 1427 (1965).

  10. Hills, I. R., and Whitehead, E. V., Nature, 209, 977 (1966).

    Article  CAS  ADS  Google Scholar 

  11. Hills, I. R., and Whitehead, E. V., Proc. Third Intern. Meet. Org. Geochem., 1966, (Pergamon, in the press.)

  12. Werner, A., Ber., 42, 4324 (1909).

    Article  Google Scholar 

  13. Boiteau, P., Pasich, B., and Ratsimamanga, Rakoto, in Les Triterpenoidsen Physiologic Végétale et Animale (Gauthier-Villars, Paris, 1964).

    Google Scholar 

  14. Budzikiewicz, H., Wilson, J. M., and Djerassi, C., J. Amer. Chem. Soc., 85, 3688 (1963).

    Article  CAS  Google Scholar 

  15. Karliner, J., and Djerassi, C., J. Org. Chem., 31, 1945 (1966).

    Article  CAS  Google Scholar 

  16. Wulfson, N. S., Zaretskii, V. I., Sadouskaya, V. L., Semenvosky, A. V., Smit, W. A., and Kucherov, V. S., Tetrahedron Lett., 22, 603 (1966).

    Article  Google Scholar 

  17. Information Bulletin No. 11, 59 (International Union of Pure and Applied Chemistry, 1960).

  18. Ruzicka, L., Proc. Chem. Soc., 341 (1959).

  19. Ruzicka, L., Eschenmoser, A., and Heusser, H., Experientia, 9, 362 (1953).

    Article  Google Scholar 

  20. Sengupta, P., and Mukhopadhyay, J., Phytochemistry, 5, 531 (1966).

    Article  CAS  Google Scholar 

  21. Sengupta, P., and Ghosh, S., J. Ind. Chem. Soc., 42, 543 (1965).

    CAS  Google Scholar 

  22. Halsall, T. G., and Aplin, R. T., Fortschritte der Chemie Organisch Naturo-stoffe, 22, 153 (1964).

    CAS  Google Scholar 

  23. Wintersteiner, O., Krakower, G., and Moore, M., J. Org. Chem., 30, 2847 (1965).

    Article  CAS  Google Scholar 

  24. Barton, D. H. R., Carruthers, W., and Overton, K. H., J. Chem. Soc., 788 (1956).

  25. Ames, T. R., Beton, J. L., Bowers, A., Halsall, T. G., and Jones, E. R. H., J. Chem. Soc., 1905 (1954). Davy, G. S., Halsall, T. G., and Jones, E. R. H., J. Chem. Soc., 2696 (1951).

  26. Hejno, K., Horák, M., Jarolim, V., Streibl, M., and Šorm, F., Chem. and Indust., 1142 (1958); Coll. Czech. Commun., 26, 459 (1961); ibid., 28, 2318 and 2443 (1963); ibid., 30, 873 (1965).

    Google Scholar 

  27. Coates, R. M., Tetrahedron Lett., 842, 4143 (1967).

    Article  Google Scholar 

  28. Nomura, M., Schleyer, von P., and Arz, A. A., J. Amer. Chem. Soc., 89, 3657 (1967).

    Article  CAS  Google Scholar 

  29. Hála, S., and Landa, S., Angew. Chem. Intern. Ed., 5, 1045 (1966).

    Article  Google Scholar 

  30. Halsall, T. G., Jones, Sir Ewart, R. H., Tan, E. L., and Chaudhry, G. R., J. Chem. Soc. (C), 1374 (1966).

  31. Kohen, F., and Stevenson, R., J. Org. Chem., 30, 2268 (1965).

    Article  CAS  Google Scholar 

  32. Pakrashi, S. C., and Samanta, T. B., Tetrahedron Lett., 38, 3679 (1967).

    Article  Google Scholar 

  33. Shoppee, C. W., and Johnston, J., J. Chem. Soc., 3261 (1961).

  34. Burgstahler, A. W., J. Amer. Chem. Soc., 79, 6047 (1957).

    Article  CAS  Google Scholar 

  35. Janot, M.-M., Devissagvet, P., Pais, M., Khuong-Huu, Q. I., Jarreau, F. X., and Goutarel, R., Bull. Soc. Chim., 4567 (1967).

  36. Row, L. R., and Rao, C. S., Tetrahedron Lett., 848, 4845 (1967).

    Article  Google Scholar 

  37. Allard, S., and Ourisson, G., Tetrahedron Lett., 1, 277 (1957).

    Article  CAS  Google Scholar 

  38. Zobell, C. E., Advances in Organic Geochemistry (edit. by Colombo, U., and Hobson, G. D.), 339 (Pergamon Press, London, 1964).

    Book  Google Scholar 

  39. Wood, E. J. F., in Microbiology of Oceans and Estuaries, 1–37 (Elsevier Publishing Company, 1967).

    Google Scholar 

  40. Levorsen, A. I., Geology of Petroleum (edit. by Gilluly, J. A., and Woodford, A. O.), second ed., 499–537 (W. H. Freeman and Company, London and San Francisco, 1967).

    Google Scholar 

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Authors and Affiliations

  1. BP Research Centre, Sunbury-on-Thames, Middlesex

    I. R. HILLS, G. W. SMITH & E. V. WHITEHEAD

Authors
  1. I. R. HILLS
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  2. G. W. SMITH
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  3. E. V. WHITEHEAD
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HILLS, I., SMITH, G. & WHITEHEAD, E. Optically Active Spirotriterpane in Petroleum Distillates. Nature 219, 243–246 (1968). https://doi.org/10.1038/219243a0

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