Abstract
The Collins/Sarett oxidation (chromium trioxide-pyridine complex), and Corey’s PCC(pyridinium chlorochromate) and PDC (pyridinium dichromate) oxidations follow a similar pathway as the Jones oxidation (chromium trioxide and sulfuric acid in acetone).
Access provided by Autonomous University of Puebla. Download to read the full chapter text
Chapter PDF
Similar content being viewed by others
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
References
Bowden, K.; Heilbron, I. M., Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39–45. Ewart R. H. (Tim) Jones worked with Ian M. Heilbron at Imperial College. Jones later succeeded Robert Robinson to become the prestigious Chair of Organic Chemistry at Manchester. The recipe for the Jones reagent: 25 g CrO3, 25 mL conc. H2SO4, and 70 mL H2O.
Ratcliffe, R. W. Org. Synth. 1973, 53, 1852.
Vanmaele, L.; De Clerq, P.; Vandewalle, M. Tetrahedron Lett. 1982, 23, 995–998.
Luzzio, F. A. Org. React. 1998, 53, 1–222. (Review).
Zhao, M.; Li, J.; Song, Z.; Desmond, R. J.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323–5326. (Catalytic CrO3 oxidation).
Waizumi, N.; Itoh, T.; Fukuyama, T. J. Am. Chem. Soc. 2000, 122, 7825–7826.
Hagiwara, H.; Kobayashi, K.; Miya, S.; Hoshi, T.; Suzuki, T.; Ando, M. Org. Lett. 2001, 3, 251–254.
Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2003, 44, 1275–1278.
Hunter, A. C.; Priest, S.-M. Steroids 2006, 71, 30–33.
Kim, D.-S.; Bolla, K.; Lee, S.; Ham, J. Tetrahedron 2013, 67, 1062–1070.
Marshall, A. J.; Lin, J.-M.; Grey, A.; Reid, I. R; Cornish, J.; Denny, W. A Bioorg Med. Chem. 2013, 21, 4112–4119.
References
Poos, G. I.; Arth, G. E.; Beyler, R. E.; Sarett, L. H. J. Am. Chem. Soc. 1953, 75, 422–429.
Collins, J. C; Hess, W. W.; Frank, F. J. Tetrahedron Lett. 1968, 3363–3366. J. C. Collins was a chemist at Sterling-Winthrop in Rensselaer, New York.
Collins, J. C; Hess, W. W. Org. Synth. 1972, Coll. Vol. V, 310.
Hill, R. K.; Fracheboud, M. G.; Sawada, S.; Carlson, R. M.; Yan, S.-J. Tetrahedron Lett. 1978, 945–948.
Krow, G. R.; Shaw, D. A.; Szczepanski, S.; Ramjit, H. Synth. Commun. 1984, 14, 429–433.
Li, M.; Johnson, M. E. Synth. Commun. 1995, 25, 533–537.
Harris, P. W. R.; Woodgate, P. D. Tetrahedron 2000, 56, 4001–4015.
Nguyen-Trung, N. Q.; Botta, O.; Terenzi, S.; Strazewski, P. J. Org. Chem. 2003, 68, 2038–2041.
Arumugam, N.; Srinivasan, P. C. Synth. Commun. 2003, 33, 2313–2320.
References
Corey, E. J.; Suggs, W. Tetrahedron Lett. 1975, 16, 2647–2650.
Bressette, A. R.; Glover, L. C., IV Synlett 2004, 738–740.
Breining, S. R.; Bhatti, B. S.; Hawkins, G. D.; Miao, L. WO2005037832 (2005).
Srikanth, G. S. C.; Krishna, U. M. Tetrahedron 2006, 62, 11165–11171.
Kim, S.-G. Tetrahedron Lett. 2008, 49, 6148–6151.
Mehta, G.; Bera, M. K. Tetrahedron 2013, 69, 1815–1821.
Fowler, K. J.; Ellis, J. L.; Morrow, G. W. Synth. Commun. 2013, 43, 1676–1682.
References
Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399–402.
Terpstra, J. W.; Van Leusen, A. M. J. Org. Chem. 1986, 51, 230–208.
Brown, H. C.; Kulkarni, S. V.; Khanna, V. V.; Patil, V. D.; Racherla, U. S. J. Org. Chem. 1992, 57, 6173–6177.
Nakamura, M.; Inoue, J.; Yamada, T. Bioorg. Med. Chem. Lett. 2000, 10, 2807–2810.
Chênevert, R. Courchene, G.; Caron, D. Tetrahedron: Asymmetry 2003, 2567–2571.
Jordão, A. K Synlett 2006, 3364–3365. (Review).
Xu, G.; Hou, A.-J.; Wang, R.-R.; Liang, G.-Y.; Zheng, Y.-T.; Liu, Z.-Y.; Li, X.-L.; Zhao, Y.; Huang, S.-X.; Peng, L.-Y.; et al. Org. Lett. 2006, 8, 4453–4456.
Morzycki, J. W; Perez-Diaz, J. O. H; Santillan, R.; Wojtkielewicz, A. Steroids 2010, 75, 70–76.
Cai, Q.; You, S.-L. Org. Lett. 2012, 14, 3040–3043.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Li, J.J. (2014). Jones oxidation. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_143
Download citation
DOI: https://doi.org/10.1007/978-3-319-03979-4_143
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-03978-7
Online ISBN: 978-3-319-03979-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)