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3,4-Dihydroisoquinolinium Trichloroacetatochromate: A Mild and Effective New Reagent for Oxidation of Alcohols to Carbonyl Compounds and Arenes to Their Quinones
Corresponding Author(s) : Recep Ozen
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
A new chromium(VI) reagent, 3,4-dihydroisoqinolinium trichloroacetatochromate was prepared by reacting trichloroacetic acid with CrO3 in water. This reagent is suitable to oxidize various primary and secondary alcohols to the corresponding carbonyl compounds and anthracene to antraquinone in a good yields.
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- Y.H. Song, Synth. Commun., 36, 631 (2006); doi:10.1080/00397910500408712.
- K. Sendil and B. Ozgün, Monatsh. Chem., 137, 1529 (2006); doi:10.1007/s00706-006-0549-2.
- B. Özgün, A. Yaylaoglu and K. Şendil, Monatsh. Chem., 138, 161 (2007); doi:10.1007/s00706-006-0574-1.
- K. Şendil and B. Ozgün, Phosphorus Sulfur Silicon Relat. Elem., 181, 959 (2006); doi:10.1080/00207450500272248.
- M.K. Chaudhuri, S.K. Dehury, S. Hussain, A. Duarah and N. Gogoi, Org. Prep. Proced. Int., 38, 331 (2006); doi:10.1080/00304940609355994.
- S. Ghammami and S. Sajadi, J. Serb. Soc, 70, 1243 (2005); doi:10.2298/JSC0511243G.
- Y.-F. Zheng, X.-F. Du and W.-L. Bao, J. Chem. Res., 2005, 753 (2005); doi:10.3184/030823405775146933
- (a) G. Cainelli and G. Cardillo Chromium Oxidation in Organic Chemistry, Springer-Verlag, Berlin, p. 118 (1984); J. Muzart, Chem. Rev., 92, 113 (1992); doi:10.1021/cr00009a005.
- J. Collins, W.W. Hess and F.J. Frank, Tetrahedron Lett., 9, 3363 (1968); doi:10.1016/S0040-4039(00)89494-0.
- (a) E.J. Corey and J.W. Suggs, Tetrahedron Lett., 16, 2647 (1975); doi:10.1016/S0040-4039(00)75204-X.; (b) E.J. Corey and G. Schmidt, Tetrahedron Lett., 20, 399 (1979); doi:10.1016/S0040-4039(01)93515-4.; (c) E. Turunc and F. Aydin, J. Org. Prep. Proc. Int., 36, 363 (2004); doi:10.1080/00304940409458680.
- K. Loonker, P.K. Sharma and K.K. Banerji, J. Chem. Res. (S), 194 (1997); doi:10.1039/A605129D.
- A. Shaabani and D.G. Lee, Synth. Commun., 33, 1845 (2003); doi:10.1081/SCC-120020194.
- M.K. Chaudhuri, K.S. Dehury, S.S. Dhar and B.U. Sinha, Synth. Commun., 34, 4077 (2004); doi:10.1081/SCC-200036584.
- (a) M.H. Hashemi, D. Ghazaanfari and M. Akhbari, Monatsh. Chem., 135, 797 (2004); (b) A. Shaabani, A. Bazgir, F. Teimouri and D.G. Lee, Tetrahedron Lett., 43, 5165 (2002); doi:10.1016/S0040-4039(02)00976-0.
- R. Ozen and A. Yurdakul, Asian J. Chem., 19, 4065 (2007).
- J.P. Heer, J.D. Harling and M. Thompson, Synth. Commun., 32, 2555 (2002); doi:10.1081/SCC-120005939.
- T.L. Allen, Anal. Chem., 30, 447 (1958); doi:10.1021/ac60135a039.
- R. Rathore, N. Saxena and S.A. Chandrasekaran, Synth. Commun., 16, 1493 (1986); doi:10.1080/00397918608056400.
- U. Bora, M.K. Chaudhuri, D. Dey, D. Kalita, W. Kharmawphlang and G.C. Mandal, Tetrahedron, 57, 2445 (2001); doi:10.1016/S0040-4020(01)00116-8.
- L.D. Ride, CRC Handbook of Chemistry and Physics, CRC Pres Inc, Physical Constants of Organic Compounds, edn 72 (1991-1992).
References
Y.H. Song, Synth. Commun., 36, 631 (2006); doi:10.1080/00397910500408712.
K. Sendil and B. Ozgün, Monatsh. Chem., 137, 1529 (2006); doi:10.1007/s00706-006-0549-2.
B. Özgün, A. Yaylaoglu and K. Şendil, Monatsh. Chem., 138, 161 (2007); doi:10.1007/s00706-006-0574-1.
K. Şendil and B. Ozgün, Phosphorus Sulfur Silicon Relat. Elem., 181, 959 (2006); doi:10.1080/00207450500272248.
M.K. Chaudhuri, S.K. Dehury, S. Hussain, A. Duarah and N. Gogoi, Org. Prep. Proced. Int., 38, 331 (2006); doi:10.1080/00304940609355994.
S. Ghammami and S. Sajadi, J. Serb. Soc, 70, 1243 (2005); doi:10.2298/JSC0511243G.
Y.-F. Zheng, X.-F. Du and W.-L. Bao, J. Chem. Res., 2005, 753 (2005); doi:10.3184/030823405775146933
(a) G. Cainelli and G. Cardillo Chromium Oxidation in Organic Chemistry, Springer-Verlag, Berlin, p. 118 (1984); J. Muzart, Chem. Rev., 92, 113 (1992); doi:10.1021/cr00009a005.
J. Collins, W.W. Hess and F.J. Frank, Tetrahedron Lett., 9, 3363 (1968); doi:10.1016/S0040-4039(00)89494-0.
(a) E.J. Corey and J.W. Suggs, Tetrahedron Lett., 16, 2647 (1975); doi:10.1016/S0040-4039(00)75204-X.; (b) E.J. Corey and G. Schmidt, Tetrahedron Lett., 20, 399 (1979); doi:10.1016/S0040-4039(01)93515-4.; (c) E. Turunc and F. Aydin, J. Org. Prep. Proc. Int., 36, 363 (2004); doi:10.1080/00304940409458680.
K. Loonker, P.K. Sharma and K.K. Banerji, J. Chem. Res. (S), 194 (1997); doi:10.1039/A605129D.
A. Shaabani and D.G. Lee, Synth. Commun., 33, 1845 (2003); doi:10.1081/SCC-120020194.
M.K. Chaudhuri, K.S. Dehury, S.S. Dhar and B.U. Sinha, Synth. Commun., 34, 4077 (2004); doi:10.1081/SCC-200036584.
(a) M.H. Hashemi, D. Ghazaanfari and M. Akhbari, Monatsh. Chem., 135, 797 (2004); (b) A. Shaabani, A. Bazgir, F. Teimouri and D.G. Lee, Tetrahedron Lett., 43, 5165 (2002); doi:10.1016/S0040-4039(02)00976-0.
R. Ozen and A. Yurdakul, Asian J. Chem., 19, 4065 (2007).
J.P. Heer, J.D. Harling and M. Thompson, Synth. Commun., 32, 2555 (2002); doi:10.1081/SCC-120005939.
T.L. Allen, Anal. Chem., 30, 447 (1958); doi:10.1021/ac60135a039.
R. Rathore, N. Saxena and S.A. Chandrasekaran, Synth. Commun., 16, 1493 (1986); doi:10.1080/00397918608056400.
U. Bora, M.K. Chaudhuri, D. Dey, D. Kalita, W. Kharmawphlang and G.C. Mandal, Tetrahedron, 57, 2445 (2001); doi:10.1016/S0040-4020(01)00116-8.
L.D. Ride, CRC Handbook of Chemistry and Physics, CRC Pres Inc, Physical Constants of Organic Compounds, edn 72 (1991-1992).