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Oxidation and Bromodehydroxymethylation of Benzylic Alcohols Using NaBrO3/NaHSO3 Reagent


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References

  1. Hollingworth, G. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Pattenden, G., Eds.; Elsevier Science Ltd.: Oxford, 1995; Vol. 3, pp 81-109.
  2. Larock, R. C. Comprehensive Organic Transformations; VCH Publishers, Inc.: New York, 1989; pp 604-614.
  3. Brink, G.-J. T.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. https://doi.org/10.1126/science.287.5458.1636
  4. Barrett, A. G. M.; Braddock, D. C.; McKinnell, R. M.; Waller, F. J. Synlett 1999, 1489.
  5. Sato, K.; Takagi, J.; Aoki, M.; Noyori, R. Tetrahedron Lett. 1998, 39, 7549. https://doi.org/10.1016/S0040-4039(98)01642-6
  6. Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419.
  7. Barhate, N. B.; Sasidharan, M.; Sudalai, A.; Wakharkar, R. D. Tetrahedron Lett. 1996, 37, 2067. https://doi.org/10.1016/0040-4039(96)00193-1
  8. Feldberg, L.; Sasson, Y. Chem. Commun. 1994, 1807.
  9. Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 539. https://doi.org/10.1016/S0040-4039(00)86883-5
  10. Yamamoto, Y.; Suzuki, H.; Moro-oka, Y. Tetrahedron Lett. 1985, 26, 2107. https://doi.org/10.1016/S0040-4039(00)94791-9
  11. Kanemoto, S.; Tomioka, H.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1986, 59, 105. https://doi.org/10.1246/bcsj.59.105
  12. Ho, T.-L. Synthesis 1978, 936.
  13. Farkas, L.; Schachter, O. J. Am. Chem. Soc. 1949, 71, 2827. https://doi.org/10.1021/ja01176a068
  14. Kajigaeshi, S.; Nakagawa, T.; Nagasaki, N.; Yamasaki, H.; Fujisaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 747. https://doi.org/10.1246/bcsj.59.747
  15. Firouzabadi, H.; Mohammadpoor-Baltork, I. Bull. Chem. Soc. Jpn. 1995, 68, 2319. https://doi.org/10.1246/bcsj.68.2319
  16. Takase, K.; Masuda, H.; Kai, O.; Nishiyama, Y.; Sakaguchi, S.; Ishii, Y. Chem. Lett. 1995, 871
  17. Ho, T.-L. Synth. Commun. 1979, 9, 237. https://doi.org/10.1080/00397917908064144
  18. Banerjee, A.; Dutt, S.; Sengupta, D.; Adak, M. M.; Samaddar, H. J. Ind. Chem. Soc. 1983, 60, 275.
  19. Adak, M. M.; Banerjee, G. C.; Banerjee, A. J. Ind. Chem. Soc. 1985, 62, 224.
  20. Banerjee, A.; Banerjee, G. C.; Bhattacharya, S.; Banerjee, S.; Samaddar, H. J. Ind. Chem. Soc. 1981, 58, 605.
  21. Adinolfi, M.; Barone, G.; Guariniello, L.; Iadonisi, A. Tetrahedron Lett. 1999, 40, 8439. https://doi.org/10.1016/S0040-4039(99)01756-6
  22. Masuda, H.; Takase, K.; Nishio, M.; Hasegawa, A.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 5550. https://doi.org/10.1021/jo00098a012
  23. Mohammadpoor-Baltork, I.; Nourozi, A. R. Synthesis 1999, 487.
  24. Groweiss, A. Org. Process Res. Dev. 2000, 4, 30. https://doi.org/10.1021/op9901947
  25. Kikuchi, D.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6023. https://doi.org/10.1021/jo972263q
  26. Sakaguchi, S.; Kikuchi, D.; Ishii, Y. Bull. Chem. Soc. Jpn. 1997, 70, 2561. https://doi.org/10.1246/bcsj.70.2561
  27. Koo, B.-S.; Lee, C. K.; Lee, K.-J. Synth. Commun. 2002, 32, 2115. https://doi.org/10.1081/SCC-120005418
  28. Bolm, C.; Magnus, A. S.; Hilderbrand, J. P. Org. Lett. 2000, 2, 1173. https://doi.org/10.1021/ol005792g
  29. Koo, B.-S.; Kim, E.-H.; Lee, K.-J. Synth. Commun. 2002, 32, 2275. https://doi.org/10.1081/SCC-120005997
  30. Elliot, M.; Janes, N. F.; Pearson, B. C. J. Sci. Food Agric. 1967, 18, 325. https://doi.org/10.1002/jsfa.2740180801
  31. Hodgson, H. H.; Beard, H. G. J. Chem. Soc. 1925, 875.
  32. Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. https://doi.org/10.1021/jo00007a031
  33. Meyers, C. Y. J. Org. Chem. 1961, 26, 1046. https://doi.org/10.1021/jo01063a018

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