Abstract
It was found that oximes undergo deoximation in the presence of the H2O2aq-HBraq system to form ketones and bromo ketones. This reaction provided the basis for the synthesis of dibromo ketones in yields varying from 40% to 94%. This method is environmentally friendly, sustainable, and easy to perform. The results of this investigation extend the potential of the use of oximes for the protection of carbonyl group, thus offering the ability to perform not only conventional deoximation but also the subsequent bromination of ketones. The reaction is easily scaled up and dibromo ketones can be prepared in gram amounts.
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C. Isart, D. Bastid, J. Burés, J. Vilarrasa, Angew. Chem. 123, 3333 (2011)
M. Hakimi, N. Feizi, H. Vahedi, H. Hassani, P.S. Thomas, Synth. Commun. 40, 725 (2010)
K. Muthu, K. Selvam, B. Krishnakumar, M. Swaminathan, Applied Cat. A: 358, 259 (2009)
X.-T. Zhou, Q.-L. Yuan, H.-B. Ji, Tetrahedron Lett. 51, 613 (2010)
E. Abele, R. Abele, L. Golomba, J. Višņevska, T. Beresneva, K. Rubina, E. Lukevics, Chem. Heterocyclic Compounds 46, 905 (2010)
N.C. Ganguly, S. Nayek, S.K. Barik, Synth. Commun. 39, 4053 (2009)
N. Jain, A. Kumar, S.M.S. Chauhan, Tetrahedron Lett. 46, 2599 (2005)
S.P. Chavan, P. Soni, Tetrahedron Lett. 45, 3161 (2004)
A. Dewan, D.K. Kakati, Asian J. Chem. 22, 2825 (2010)
A.O. Terent’ev, I.B. Krylov, Y.N. Ogibin, G.I. Nikishin, Synthesis, 3819 (2006)
A. Podgoršek, M. Zupan, J. Iskra, Angew. Chem. Int. Ed. 48, 8424 (2009)
M. Eissen, D. Lenoir, Chem. A Europ. J. 14, 9830 (2008)
N.B. Barhate, A.S. Gajare, R.D. Wakharkar, A.V. Bedekar, Tetrahedron 55, 11127 (1999)
N.B. Barhate, A.S. Gajare, R.D. Wakharkar, A.V. Bedekar, Tetrahedron Lett. 39, 6349 (1998)
U. Bora, G. Bose, M.K. Chaudhuri, S.S. Dhar, R. Gopinath, A.T. Khan, B.K. Patel, Org. Lett. 2, 247 (2000)
N.I. Rudakova, O.V. Anufrieva, E.A. Smirnova, J. Gen. Chem. USSR (Engl. Transl.) 62, 1887 (1992); Zh. Obshch. Khim. 62, 2290 (1992) (In Russian)
N.I. Rudakova, Yu.G. Erykalov, S.M. Zharikova, E.V. Dmitrieva, M.S. Mataradze, Russ. J. Gen. Chem. 65, 271 (1995); Zh. Obshch. Khim. 65, 315 (1995)
J. Dakka, Y. Sasson, J. Chem. Soc. Chem. Commun. 1421 (1987)
B.S. Bhatkhande, M.V. Adhikari, S.D. Samant, Ultrasonics Sonochemistry 9, 31 (2002)
P.V. Vyas, A.K. Bhatt, G. Ramachandraiah, A.V. Bedekar, Tetrahedron Lett. 44, 4085 (2003)
P. Bezodis, J.R. Hanson, P. Petit, J. Chem.Res.Synop. 7, 334 (1996)
A.M. Andrievskii, M.V. Gorelik, S.V. Avidon, E.Sh. Al’tman, Russ. J. Org. Chem. 29, 1519 (1993); Zh. Org. Khim. 29, 1828 (1993) (In Russian)
S. Mukhopadhyay, S. Ananthakrishnan, S.B. Chandalia, Org. Process Res. Dev. 3, 10 (1999); 3, 196 (1999); 3, 451 (1999)
V.S. Arutyunyan, T.V. Kochikyan, N.S. Egiazaryan, A.A. Avetisyan, Russ. J. Org. Chem. 31, 90 (1995); Zh.Org.Khim. 31, 100 (1995) (In Russian)
T. Moriuchia, M. Yamaguchia, K. Kikushimaa, T. Hirao, Tetrahedron Lett. 48, 2667 (2007)
A.O. Terent’ev, S.V. Khodykin, N.A. Troitskii, Yu.N. Ogibin, G.I. Nikishin, Synthesis 2845 (2004)
A.O. Terent’ev, S.V. Khodykin, I.B. Krylov, Yu.N. Ogibin, G.I. Nikishin, Synthesis 1087 (2006)
V.H. Tillu, P.D. Shinde, A.V. Bedekar, R.D. Wakharkar, Synth. Commun. 33, 1399 (2003)
A. Podgoršek, S. Stavber, M. Zupan, J. Iskra, Green Chem. 9, 1212 (2007)
A. Podgoršek, S. Stavber, M. Zupan, J. Iskra, Tetrahedron 65, 4429 (2009)
A. Amati, G. Dosualdo, L.H. Zhao, A. Bravo, F. Fontana, F. Minisci, H.R. Bjorsvik, Org. Process Res. Dev. 2, 261 (1998)
J.H. Espenson, Z. Zhu, T.H. Zauche, J. Org. Chem. 64, 1191 (1999)
V.B. Sharma, S.L. Jain, B. Sain, Synlett 173 (2005)
R. Taylor, Electrophilic Aromatic Substitution (John Wiley & Sons, New York, 1990)
B.R. Kim, H.-G. Lee, E.J. Kim, S.-G. Lee, Y.-J. Yoon, J. Org. Chem. 75, 484 (2010)
A.R. Hajipour, A.E. Ruoho, S. Safaei, Synthetic Commun. 39, 3687 (2009)
V.F. Traven, B.I. Stepanov, J. Org. Chem. USSR (English Translation) 5, 1756 (1969); Zh. Org. Khim 5, 1809 (1969) (In Russian)
V.P. Krawez, G.I. Chervenyuk, G.V. Grinev, J.Org.Chem.USSR (Engl.Transl.) 2, 1238 (1966); Zh.Org.Khim. 2, 1244 (1966) (In Russian)
K.G. Rutherford, C.L. Stevens, J. Am. Chem. Soc. 77, 3278 (1955)
S. Paul, V. Gupta, R. Gupta, A. Loupy, Tetrahedron Lett. 44, 439 (2003)
K. Kim, J. Cho, S.C. Yoon, J. Chem. Soc. Perkin Trans. 1, 253 (1995)
J.-M. Poirier, Bull. Soc. Chim. Fr. 2, 17 (1982)
S. Koenig, I. Ugi, H. Schramm, J.Arch.Pharm. (Weinheim, Germany) 328, 699 (1995)
R. Breslow, L.J. Altman, A. Krebs, E. Mohacsi, I. Murata, R.A. Peterson, J. Posner, J. Am. Chem. Soc. 87, 1326 (1965)
A.W. Erian, S.M. Sherif, H.M. Gaber, Molecules 8, 793 (2003)
A.L. Wilds, C. Djerassi, J. Am. Chem. Soc. 68, 2125 (1946)
E.R. Blout, V.W. Eager, D.C. Silverman, J. Am. Chem. Soc. 68, 566 (1946)
A. Podgoršek, M. Eissen, J. Fleckenstein, S. Stavber, M. Zupan, J. Iskra, Green Chem. 11, 120 (2009)
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Terent’ev, A.O., Krylov, I.B., Vil’, V.A. et al. Synthesis of dibromo ketones by the reaction of the environmentally benign H2O2-HBr system with oximes. cent.eur.j.chem. 10, 360–367 (2012). https://doi.org/10.2478/s11532-011-0158-8
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DOI: https://doi.org/10.2478/s11532-011-0158-8