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Selective Oxidations of Secondary Alcohols in Presence of Primary Alcohols

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Oxidation of Alcohols to Aldehydes and Ketones

Part of the book series: Basic Reactions in Organic Synthesis ((BROS))

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Section 10.1. References

  1. See, for example: (a) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H.; Tetrahedron Lett. 1981, 22, 1605. (b) Tietze, L. F.; Henke, S.; Bärtels, C.; Tetrahedron 1988, 44, 7145.

    Article  CAS  Google Scholar 

  2. Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H.; Tetrahedron Lett. 1981, 22, 1605.

    Article  CAS  Google Scholar 

  3. Fétizon, M.; Golfier, M.; Louis, J.-M.; J. Chem. Soc., Chem. Commun. 1969, 1102.

    Google Scholar 

  4. See, for example: Kurth, M. J.; Yu, C.-M.; J. Org. Chem. 1985, 50, 1840.

    Article  CAS  Google Scholar 

Section 10.2. References

  1. Reich, H.; Reichstein, T.; Helv. Chim. Acta 1943, 26, 562.

    Article  CAS  Google Scholar 

  2. See, for example: (a) Sarett, L. H.; J. Am. Chem. Soc. 1949, 71, 1165. (b) Fieser, L. F.; Rajagopalan, S.; J. Am. Chem. Soc. 1950, 72, 5530. (c) Chemerda, J. M.; Chamberlain, E. M.; Wilson, E. H.; Tishler, M.; J. Am. Chem. Soc. 1951, 73, 4052. (d) Hanze, A. R.; Fonken, G. S.; McIntosh Jr., A. V.; Searcy, A. M.; Levin, R. H.; J. Am. Chem. Soc. 1954, 76, 3179.

    Article  CAS  Google Scholar 

  3. Kritchevsky, T. H.; Garmaise, D. L.; Gallagher, T. F.; J. Am. Chem. Soc. 1952, 74, 483.

    Article  CAS  Google Scholar 

  4. Jones, R. E.; Kocher, F. W.; J. Am. Chem. Soc. 1954, 76, 3682.

    CAS  Google Scholar 

  5. See, for example: (a) Johnson, W. S.; Collins Jr., J. C.; Pappo, R.; Rubin, M. B.; Kropp, P. J.; Johns, W. F.; Pike, J. E.; Bartmann, W.; J. Am. Chem. Soc. 1963, 85, 1409. (b) Murahashi, S.-Ichi; Saito, T.; Hanaoka, H.; Murakami, Y.; Naota, T.; Kumobayashi, H.; Akutagawa, S.; J. Org. Chem. 1993, 58, 2929.

    Article  CAS  Google Scholar 

  6. Stevens, R. V.; Chapman, K. T.; Weller, H. N.; J. Org. Chem. 1980, 45, 2030.

    Article  CAS  Google Scholar 

  7. Stevens, R. V.; Chapman, K. T.; Tetrahedron Lett. 1982, 23, 4647.

    Google Scholar 

  8. See, for example: (a) Lehmann, J.; Scheuring, M.; Lieb. Ann. Chem. 1990, 3, 271. (b) Skarzewski, J.; Siedlecka, R.; Org. Prep. Proc. Int. 1992, 24, 623. (c) Corey, E. J.; Lazerwith, S. E.; J. Am. Chem. Soc. 1998, 120, 12777.

    Google Scholar 

  9. (a) Wicha, J.; Zarecki, A.; Tetrahedron Lett. 1974, 3059. (b) Tassignon, P. S. G.; de Wit, D.; de Rijk, T. C.; De Buyck, L. F.; Tetrahedron 1995, 51, 11863. (c) Al Neirabeyer, M.; Ziegler, J.-C.; Gross, B.; Caubére, P.; Synthesis 1976, 811.

    Google Scholar 

  10. (a) Hiegel, G. A.; Nalbandy, M.; Synth. Commun. 1992, 22, 1589. (b) Tassignon, P. S. G.; de Wit, D.; de Rijk, T. C.; De Buyck, L. F.; Tetrahedron 1995, 51, 11863.

    CAS  Google Scholar 

  11. Rozen, S.; Bareket, Y.; Kol, M.; Tetrahedron 1993, 49, 8169.

    Article  CAS  Google Scholar 

  12. Schlama, T.; Gabriel, K.; Gouverneur, V.; Mioskowski, C.; Angew. Chem. Int. Ed. 1997, 36, 2342.

    Article  CAS  Google Scholar 

  13. Kolthoff, I. M.; Belcher, R.; Volumetric Analysis III; Interscience Publishers, Inc., New York, 1957, p. 262.

    Google Scholar 

Section 10.3. References

  1. David, S.; C. R. Acad. Sc. Paris (C) 1974, 278, 1051.

    CAS  Google Scholar 

  2. (a) Saigo, K.; Morikawa, A.; Mukaiyama, T.; Chem. Lett. 1975, 145. (b) Saigo, K.; Morikawa, A.; Mukaiyama, T.; Bull. Chem. Soc. Jpn. 1976, 49, 1656.

    Google Scholar 

  3. (a) Morikawa, A.; Mukaiyama, T.; Bull. Chem. Soc. Jpn. 1976, 49, 1656 Ref. 19b. (b) Ogawa, T.; Matsui, M.; J. Am. Chem. Soc. 1976, 98, 1629.

    CAS  Google Scholar 

  4. (a) Matsui, M.; J. Am. Chem. Soc. 1976, 98, 1629 Ref. 20b. (b) Kong, X.; Grindley, T. B.; J. Carbohydr. Chem. 1993, 12, 557.

    Article  CAS  Google Scholar 

  5. (a) David, S.; Thieffry, A.; J. Chem. Soc., Perkin Trans. I 1979, 1568. (b) Ref. 19b.

    Google Scholar 

  6. (a) Thieffry, A.; J. Chem. Soc., Perkin Trans. I 1979, 1568 Ref. 22a. (b) Ref. 19b. (c) Furneaux, R. H.; Gainsford, G. J.; Lynch, G. P.; Yorke, S. C.; Tetrahedron 1993, 49, 9605.

    Google Scholar 

  7. (a) Thieffry, A.; J. Chem. Soc., Perkin Trans. I 1979, 1568 Ref.22a. (b) Tsuda, Y.; Matsuhira, N.; Kanemitsu, K.; Chem. Pharm. Bull. 1985, 33, 4095. (c) Tsuda, Y.; Hanajima, M.; Matsuhira, N.; Okuno, Y.; Kanemitsu, K.; Chem. Pharm. Bull. 1989, 37, 2344.

    Google Scholar 

  8. Ueno, Y.; Okawara, M.; Tetrahedron Lett. 1976, 4597.

    Google Scholar 

  9. See, for example: White, J. D.; Jensen, M. S.; J. Am. Chem. Soc. 1995, 117, 6224.

    Article  CAS  Google Scholar 

  10. D’Andrea, F.; Catelani, G.; Mariani, M.; Vecchi, B.; Tetrahedron Lett. 2001, 42, 1139.

    Article  CAS  Google Scholar 

Section 10.4. References

  1. Ishii, Y.; Yamawaki, K.; Yoshida, T.; Ura, T.; Ogawa, M.; J. Org. Chem. 1987, 52, 1868.

    Article  CAS  Google Scholar 

  2. Yamawaki, K.; Nishihara, H.; Yoshida, T.; Ura, T.; Yamada, H.; Ishii, Y.; Ogawa, M.; Synth. Commun. 1988, 18, 869.

    CAS  Google Scholar 

  3. Trost, B. M.; Masuyama, Y.; Tetrahedron Lett. 1984, 25, 173.

    Article  CAS  Google Scholar 

  4. Masuyama, Y.; Takahashi, M.; Kurusu, Y.; Tetrahedron Lett. 1984, 25, 4417.

    Article  CAS  Google Scholar 

  5. Yamawaki, K.; Yoshida, T.; Suda, T.; Ishii, Y.; Ogawa, M.; Synthesis 1986, 59.

    Google Scholar 

  6. Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M.; J. Org. Chem. 1988, 53, 3587.

    Article  CAS  Google Scholar 

  7. (a) Sakata, Y.; Ishii, Y.; J. Org. Chem. 1991, 56, 6233. (b) Dakin, L. A.; Langille, N. F.; Panek, J. S.; J. Org. Chem. 2002, 67, 6812.

    Article  CAS  Google Scholar 

  8. (a) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R.; J. Am. Chem. Soc. 1997, 119, 12386. (b) Bogdał, D.; Łukasiewicz, M.; Synlett 2000, 1, 143.

    Article  CAS  Google Scholar 

  9. Firouzabadi, H.; Iranpoor, N.; Amani, K.; Synthesis 2003, 3, 408.

    Article  Google Scholar 

  10. (a) Tomioka, H.; Oshima, K.; Nozaki, H.; Tetrahedron Lett. 1982, 23, 539. (b) Kanemoto, S.; Tomioka, H.; Oshima, K.; Nozaki, H.; Bull. Chem. Soc. Jpn. 1986, 59, 105. (c) Banerjee, A. K.; Peña-Matheud, C. A.; de Carrasco, M. C.; J. Chem. Soc., Perkin Trans. I 1988, 8, 2485.

    Article  CAS  Google Scholar 

  11. (a) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H.; Tetrahedron Lett. 1984, 25, 3317. (b) Kanemoto, S.; Saimoto, H.; Oshima, K.; Utimoto, K.; Nozaki, H.; Bull. Chem. Soc. Jpn. 1989, 62, 519.

    Article  CAS  Google Scholar 

  12. Shaabani, A.; Lee, D. G.; Synth. Commun. 2003, 33, 1845.

    Article  CAS  Google Scholar 

  13. Kaneda, K.; Kawanishi, Y.; Jitsukawa, K.; Teranishi, S.; Tetrahedron Lett. 1983, 24, 5009.

    Article  CAS  Google Scholar 

  14. Arterburn, J. B.; Liu, M.; Perry, M. C.; Helv. Chim. Acta 2002, 85, 3225.

    Article  CAS  Google Scholar 

  15. Martín, S. E.; Suárez, D. F.; Tetrahedron Lett. 2002, 43, 4475.

    Article  Google Scholar 

  16. Bovicelli, P.; Lupattelli, P.; Sanetti, A.; Mincione, E.; Tetrahedron Lett. 1994, 35, 8477.

    Article  CAS  Google Scholar 

  17. Matsushita, T.; Ebitani, K.; Kaneda, K.; Chem. Commun. 1999, 3, 265.

    Article  Google Scholar 

  18. Nishiguchi, T.; Asano, F.; Tetrahedron Lett. 1988, 29, 6265.

    Article  CAS  Google Scholar 

  19. Soo Kim, K.; Heon Song, Y.; Lee, N. H.; Hahn, C. S.; Tetrahedron Lett. 1986, 27, 2875.

    Article  Google Scholar 

  20. Soo Kim, K.; Chung, S.; Haeng Cho, I.; Hahn, C. S.; Tetrahedron Lett. 1989, 30, 2559.

    Article  Google Scholar 

  21. Posner, G. H.; Perfetti, R. B.; Runquist, A. W.; Tetrahedron Lett. 1976, 3499.

    Google Scholar 

  22. (a) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H.; Tetrahedron Lett. 1981, 22, 1605. (b) Takai, K.; Oshima, K.; Nozaki, H.; Tetrahedron Lett. 1980, 21, 1657.

    Article  CAS  Google Scholar 

  23. Soo Kim, K.; Haeng Cho, I.; Ki Yoo, B.; Heon Song, Y.; Sun Hahn, C.; J. Chem. Soc., Chem.Commun. 1984, 762.

    Google Scholar 

  24. (a) Kageyama, T.; Kawahara, S.; Kitamura, K.; Ueno, Y.; Okawara, M.; Chem. Lett. 1983, 1097. (b) Morimoto, T.; Hirano, M.; Iwasaki, K.; Ishikawa, T.; Chem. Lett. 1994, 1, 53.

    Google Scholar 

  25. (a) Shaabani, A.; Ameri, M.; J. Chem. Res. (S) 1998, 2, 100. (b) Shaabani, A.; Lee, D. G.; Synth. Commun. 2003, 33, 1255.

    Article  Google Scholar 

Section 10.5 References

  1. (a) Nonaka, T.; Kanemoto, S.; Oshima, K.; Nozaki, H.; Bull. Chem. Soc. Jpn. 1984, 57, 2019. (b) See, for example: Kurth, M. J.; Yu, C.-M.; J. Org. Chem. 1985, 50, 1840.

    CAS  Google Scholar 

  2. Jung, M. E.; Brown, R. W.; Tetrahedron Lett. 1978, 2771.

    Google Scholar 

  3. Jung, M. E.; Speltz, L. M.; J. Am. Chem. Soc. 1976, 98, 7882.

    Article  CAS  Google Scholar 

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(2006). Selective Oxidations of Secondary Alcohols in Presence of Primary Alcohols. In: Oxidation of Alcohols to Aldehydes and Ketones. Basic Reactions in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/0-387-25725-X_10

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