Phase-transfer-catalysed Ring Opening of Cyclohexene Oxide by Phenylacetonitrile Carbanion in the Presence of Lithium Salts†

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Rado Marković, Goran Dimitrijević and Vesna Aleksić


Abstract

Lithium cation assisted nucleophilic ring opening of cyclohexene oxide, by phenylacetonitrile carbanions, under phase-transfer conditions giving rise to a diastereoisomeric mixture of trans-γ-hydroxynitriles 7 and 8 is reported.


References

  1. G. Stork, L. D. Cama and D. R. Coulson, J. Am. Chem. Soc., 1974, 96, 5268 CrossRef CAS.
  2. M. Mousseron and M. Canet, Bull. Soc. Chim. Fr., 1952, 190 CAS.
  3. F. G. Bordwell, Acta. Chem. Res., 1988, 21, 456 Search PubMed.
  4. E. M. Kaiser and C. R. Hauser, J. Org. Chem., 1968, 33, 3402 CrossRef CAS.
  5. M. Makosza and A. Jonczyk, Org. Synth., 1976, 55, 91 CAS.
  6. J. Jarrousse and J.-C. Raulin, C.R. Acad. Sci. Paris, Ser. C, 1977, 284, 503 Search PubMed.
  7. M. Fedorynski, K. Wopciechowski, Z. Matacz and M. Makosza, J. Org. Chem., 1978, 43, 4682 CrossRef CAS.
  8. W. Lasek and M. Makosza, Synthesis, 1993, 780 CrossRef CAS.
  9. A. Jonczyk, T. Kulinski, M. Czupryniak and P. Balcerzak, Synlett, 1991, 639 CrossRef CAS.
  10. D. Abenhaïm, A. Loupy, C. Mahieu and D. Séméria, Synth. Commun., 1994, 24, 1809.
  11. M. Makosza and M. Fedorrynski, Adv. Catal., 1987, 375 CAS.
  12. C. J. Chang, R. F. Kiesel and T. E. Hogen-Esch, J. Am. Chem. Soc., 1973, 95, 8446 CrossRef CAS.
  13. D. Albanese, D. Landini and M. Penso, Synthesis, 1994, 34 CrossRef CAS.
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