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Favorskii rearrangement

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Abstract

Transformation of enolizable α-haloketones to esters, carboxylic acids, or amides via alkoxide-, hydroxide-, or amine-catalyzed rearrangements, respectively.

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References

  1. (a) Favorskii, A. E. J. Prakt. Chem. 1895, 51, 533–563. Aleksei E. Favorskii (1860–1945), born in Selo Pavlova, Russia, studied at St. Petersburg State University, where he became a professor since 1900. (b) Favorskii, A. E. J. Prakt. Chem. 1913, 88, 658.

    Google Scholar 

  2. Wagner, R. B.; Moore, J. A. J. Am. Chem. Soc. 1950, 72, 3655–3658.

    Article  CAS  Google Scholar 

  3. Wenkert, E.; Bakuzis, P.; Baumgarten, R. J.; Leicht, C. L.; Schenk, H. P. J. Am. Chem. Soc. 1971, 93, 3208–3216.

    Article  CAS  Google Scholar 

  4. Chenier, P. J. J. Chem. Ed. 1978, 55, 286–291. (Review).

    Google Scholar 

  5. Barreta, A.; Waegell, B. In Reactive Intermediates; Abramovitch, R. A., ed.; Plenum Press: New York, 1982, 2, pp 527–585. (Review).

    Google Scholar 

  6. White, J. D.; Dillon, M. P.; Butlin, R. J. J. Am. Chem. Soc. 1992, 114, 9673–9674.

    Article  CAS  Google Scholar 

  7. Dhavale, D. D.; Mali, V. P.; Sudrik, S. G.; Sonawane, H. R. Tetrahedron 1997, 53, 16789–16794.

    Article  CAS  Google Scholar 

  8. Kitayama, T.; Okamoto, T. J. Org. Chem. 1999, 64, 2667–2672.

    Article  CAS  Google Scholar 

  9. Mamedov, V. A.; Tsuboi, S.; Mustakimova, L. V.; Hamamoto, H.; Gubaidullin, A. T.; Litvinov, I. A.; Levin, Y. A. Chem. Heterocyclic Compd. 2001, 36, 911. (Review).

    Google Scholar 

  10. Harmata, M.; Wacharasindhu, S. Org. Lett. 2005, 7, 2563–2565.

    Article  CAS  Google Scholar 

  11. Pogrebnoi, S.; Saraber, F. C. E.; Jansen, B. J. M.; de Groot, A. Tetrahedron 2006, 62, 1743–1748.

    Article  CAS  Google Scholar 

  12. Filipski, K.J.; Pfefferkorn, J. A. Favorskii Rearrangement. In Name Reactions for Homologations-Part II; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 238–252. (Review).

    Google Scholar 

  13. Kammath, V. B.; Šolomek, T.; Ngoy, B. P.; Heger, D.; Klán, P.; Rubina, M.; Givens, R. S. J. Org. Chem. 2013, 78, 1718–1729.

    Article  CAS  Google Scholar 

References

  1. Cope, A. C.; Graham, E. S. J. Am. Chem. Soc. 1951, 73, 4702–4706.

    Article  CAS  Google Scholar 

  2. Smissman, E. E.; Diebold, J. L. J. Org. Chem. 1965, 30, 4005–4007.

    Article  CAS  Google Scholar 

  3. Sasaki, T.; Eguchi, S.; Toru, T. J. Am. Chem. Soc. 1969, 91, 3390–3391.

    Article  CAS  Google Scholar 

  4. Baudry, D.; Begue, J. P.; Charpentier-Morize, M. Tetrahedron Lett. 1970, 2147–2150.

    Google Scholar 

  5. Stevens, C. L.; Pillai, P. M.; Taylor, K. G. J. Org. Chem. 1974, 39, 3158–3161.

    Article  CAS  Google Scholar 

  6. Harmata, M.; Wacharasindhu, S. J. Org. Chem. 2005, 70, 725–728.

    Article  CAS  Google Scholar 

  7. Filipski, K.J.; Pfefferkorn, J. A. Favorskii Rearrangement. In Name Reactions for Homologations-Part II; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 438–452. (Review).

    Google Scholar 

  8. Harmata, M.; Wacharasindhu, S. Synthesis 2007, 2365–2369.

    Google Scholar 

  9. Ross, A. G.; Townsend, S. D.; Danishefsky, S. J. J. Org. Chem. 2013, 78, 204–210.

    Article  CAS  Google Scholar 

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Li, J.J. (2014). Favorskii rearrangement. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_100

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