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Vol. 31 No. 12 (2019): Vol 31 Issue 12

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Dilithium Tetrachloromanganate an Effective Reagent for Regioselective Ring Opening of Epoxides with Grignard Reagents

https://doi.org/10.14233/ajchem.2019.22270
Santosh S. Devkate
Department of Chemistry, Rayat Sikshan Sanstha’s S.M. Joshi College, Hadapsar, Pune-411028, India
https://orcid.org/0000-0001-7787-023X
Arvind S. Burungale
Department of Chemistry, Rayat Sikshan Sanstha’s S.M. Joshi College, Hadapsar, Pune-411028, India
Ashok S. Pise
Department of Chemistry, Rayat Sikshan Sanstha’s S.M. Joshi College, Hadapsar, Pune-411028, India

Corresponding Author(s) : Arvind S. Burungale

asburungale@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 12 (2019): Vol 31 Issue 12

Abstract

The epoxides were obtained from substituted phenols and epichlorohydrin by reported methods. The regioselective ring opening of epoxides were studied in different solvents by reaction with Grignard’s reagent in presence of dilithium tetrachloromanganate.

Keywords

Epoxide Epichlorohydrin Regioselective Grignard Transmetallation
Devkate, S. S., Burungale, A. S., & Pise, A. S. (2019). Dilithium Tetrachloromanganate an Effective Reagent for Regioselective Ring Opening of Epoxides with Grignard Reagents. Asian Journal of Chemistry, 31(12), 2841–2845. https://doi.org/10.14233/ajchem.2019.22270
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References
  1. M. Bartok and K.L. Lang, In the Chemistry of Heterocyclic Compounds; Hassner A.; Ed; Wiley: New York, vol. 42, Part 3, Chapter 1 (1985).
  2. J.G. Smith, Synthesis, 629 (1984); https://doi.org/10.1055/s-1984-30921.
  3. M.J. Orchin, Chem. Educ., 66, 586 (1989); https://doi.org/10.1021/ed066p586.
  4. A. Rosowsky, ed.: A. Weissberger, Chemistry of Heterocyclic Compounds, Wiley: New York, vol. 19, Part 1, Chap. 1 (1964).
  5. M. Tiffeneau and E.C.R. Fourneau, Acad. Sci., 146, 697 (1908).
  6. J. Deniau, E. Henry-Basch and P. Freon, Bull. Soc. Chim. Fr., 4414 (1969).
  7. T. Katsuki and K.B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980); https://doi.org/10.1021/ja00538a077.
  8. K.B. Sharpless, C.H. Behrens, T. Katsuki, A.W.M. Lee, V.S. Martin, M. Takatani, S.M. Viti, F.J. Walker and S.S. Woodard, Pure Appl. Chem., 55, 589 (1983); https://doi.org/10.1351/pac198855040589.
  9. M.R. Johnson, T. Nakata and Y. Kishi, Tetrahedron Lett., 20, 4343 (1979); https://doi.org/10.1016/S0040-4039(01)86584-9.
  10. T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima and H. Nozaki, Tetrahedron, 23, 3597 (1982); https://doi.org/10.1016/S0040-4039(00)87680-7.
  11. M. Caron and K.B. Sharpless, J. Org. Chem., 50, 1557 (1985); https://doi.org/10.1021/jo00209a047.
  12. T. Mukaiyama, K. Soai, T. Sato, H. Shimizu and K. Suzuki, J. Am. Chem. Soc., 101, 1455 (1979); https://doi.org/10.1021/ja00500a015.
  13. J. Whitesell and S.W. Felman, J. Org. Chem., 45, 755 (1980); https://doi.org/10.1021/jo01292a055.
  14. G. Posner, Org. React., 22, 253 (1975).
  15. N.G. Gaylord and E.L. Becker, Chem. Rev., 49, 413 (1951); https://doi.org/10.1021/cr60154a001.
  16. R.W. Herr, D.M. Wieland and C.R. Johnson, J. Am. Chem. Soc., 92, 3813 (1970); https://doi.org/10.1021/ja00715a060.
  17. S.C. Bergmeier and D.J. Lapinsky, Prog. Heterocycl. Chem., 25, 47 (2013).
  18. G. Boireau, D. Abenhaim, J.L. Namy and E. Henry-Basch, Z. Org. Khim., 12, 1841 (1976).
  19. B.J. Wakefield, Chemistry of Organolithium Compounds, Pergamon Press: Oxford (1974).
  20. M.S. Karash and O. Reinmuth, Grignard Reactions of Non-Metallic Substances, Prentice Hall: New York (1954).
  21. R.E. Parker and N.S. Isaacs, Chem. Rev., 59, 737 (1959); https://doi.org/10.1021/cr50028a006.
  22. N.G. Gaylord and E.I. Becker, Chem. Rev., 2, 413 (1951); https://doi.org/10.1021/cr60154a001.
  23. H. Yi, D. Yang, J. Xin, X. Qi, Y. Lan, Y. Deng, C.-W. Pao, J.-F. Lee and A. Lei, Nature Commun., 8, Article number: 14794 (2017); https://doi.org/10.1038/ncomms14794.
  24. G.E. Posner, An Introduction to Synthesis Using Organocopper Reagents, John Wiley & Sons, New York (1980).
  25. W.H. Mandeville and G.M. Whitesides, J. Org. Chem., 39, 400 (1974); https://doi.org/10.1021/jo00917a027.
  26. B.E. Lipshutz, R.S. Wilhelm and J.A. Kozlowski, Tetrahedron Lett., 23, 3755 (1982); https://doi.org/10.1016/S0040-4039(00)87698-4.
  27. S.F. Martin, Tetrahedron, 36, 419 (1980); https://doi.org/10.1016/0040-4020(80)80024-X.
  28. K. Fuji, Chem. Rev., 93, 2037 (1993); https://doi.org/10.1021/cr00022a005.
  29. E.J. Corey and A. Guzman-Perez, Angew. Chem. Int. Ed., 37, 388 (1998); https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO;2-V.
  30. S. Takano, Y. Imamura and K. Ogasawara, Tetrahedron Lett., 22, 4479 (1981); https://doi.org/10.1016/S0040-4039(01)93019-9.
  31. D.E. Frantz, R. Fässler and E.M. Carreira, J. Am. Chem. Soc., 122, 1806 (2000); https://doi.org/10.1021/ja993838z.
  32. B.M. Trost, A.H. Weiss and A. Jacobi von Wangelin, J. Am. Chem. Soc., 128, 8 (2006); https://doi.org/10.1021/ja054871q.
  33. B.M. Trost, A.C. Burns, M.J. Bartlett, T. Tautz and A.H. Weiss, J. Am. Chem. Soc., 134, 1474 (2012); https://doi.org/10.1021/ja210986f.
  34. D.S. Lee, C.W. Gau, Y.Y. Chen and T.J. Lu, Appl. Organomet. Chem., 30, 242 (2016); https://doi.org/10.1002/aoc.3423.
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