Ultrasound assisted the chemoselective 1,1-diacetate protection and deprotection of aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate salt as a eco-benign, efficient and reusable solid acid catalyst

Ultrasonics Sonochemistry

Volumn 20, Issue 1, 2013, Pages 19-25

  Khaligh, Nader Ghaffari ^a   Shirini, Farhad ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

1,1 Diacetylation; Aldehydes; Poly(4 vinyl pyridine); Solid acid; Solvent free; Ultrasonic irradiation

Indexed keywords

ALDEHYDES; IRRADIATION; ORGANIC SOLVENTS; SULFUR COMPOUNDS; ULTRASONICS;

1 ,1-DIACETYLATION; POLY(4-VINYL PYRIDINE); SOLID ACID; SOLVENT FREE; ULTRASOUND IRRADIATION;

CATALYSTS;

1,1 DIACETATE DERIVATIVE; ACETOACETIC ACID DERIVATIVE; ALDEHYDE; POLY(4 VINYLPYRIDINIUM)HYDROGEN SULFATE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DEACYLATION; ELECTRON TRANSPORT; GREEN CHEMISTRY; IRRADIATION; ISOLATION AND PURIFICATION; PRIORITY JOURNAL; REACTION TIME; ROOM TEMPERATURE; ULTRASOUND;

EID: 84867742501     PISSN: 13504177     EISSN: 18732828     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2012.07.016     Document Type: Article

References (95)

1. S.C. Stinson Chem. Eng. 74 1996 39
2. K. Tanaka, and F. Toka Chem. Rev. 100 2000 1025
3. A.J. Fatiadi, Synthesis 1987, 85.
4. F.M. Menger, and C. Lee J. Org. Chem. 44 1979 3446 3448
5. K. Smith Solid Supports and Catalysis in Organic Synthesis 1992 Ellis Horwood and PTR Prentice Hall New York
6. P. Laszlo, Comprehensive Organic Synthesis, vol. 7. Trost, B.M. (Ed.), Pergamon, New York, (1991) pp. 839.
7. D. Choudhary, S. Paul, R. Gupta, and J.H. Clark Green Chem. 8 2006 479
8. A. Ghorbani-Choghamarani, and S. Sardari J. Sulfur Chem. 32 2011 63
9. R. Dalpozzo, G. Bartoli, L. Sambri, and P. Melchiorre Chem. Rev. 110 6 2010 3501
10. A.K. Chakraborti, B. Singh, S.V. Chankeshwara, and A.R. Patel J. Org. Chem. 74 16 2009 5967
11. G. Sharma, R. Kumar, and A.K. Chakraborti Tetrahedron Lett. 49 2008 4272
12. B. Karimi, and M. Khalkhali J. Mol. Catal. A: Chem. 232 2005 113
13. K. Niknam, D. Saberi, and M. Nouri Sefat Tetrahedron Lett. 50 2009 4058
14. K. Tanabe, and W.F. Hölderich Appl. Catal. A 181 1999 399
15. J.A. Melero, R. van Grieken, and G. Morales Chem. Rev. 106 2006 3790
16. A. Akelah, and D.C. Sherindton Chem. Rev. 81 1981 557
17. D.C. Sherington, and P. Hodge Synthesis and Separation Using Functional Polymers 1988 Wiley Chichester
18. K. Takemoto, Y. Inaki, and R.M. Ottenbrite Functional Monomers and Polymers 1987 Dekker New York
19. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, and S.J. Taylor J. Chem. Soc. Perkin Trans. 1 2000 3815
20. V. Rao, P.V. Ashokan, and M.H. Shridhar Mat. Sci. Eng. A 276 2000 266
21. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis third ed. 1999 John Wiley and Sons New York
22. M.J. Gregory J. Chem. Soc. B 1970 1201
23. F.R. Heerden, J.J. Huyser, D.B.G. Williams, and C.W. Holzapfer Tetrahedron Lett. 39 1998 5281
24. B.M. Trost, and C. Lee J. Am. Chem. Soc. 123 2001 12191
25. M. Sandberg, and L.K. Sydnes Tetrahedron Lett. 39 1998 6361
26. K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Rajadhyaksha, and H.W. Pinnick Protecting groups in organic synthesis. Part 8. Conversion of aldehydes into 1,1-diacetates J. Org. Chem. 48 1983 1765
27. M. Tomita, T. Kikuchi, K. Bessho, T. Hori, and Y. Inubushi Chem. Pharm. Bull. 11 1963 1484
28. R. Wegscheider, and E. Spath Monatsh. Chem. 30 1909 825
29. W. Davey, and J.R. Gwilt J. Chem. Soc. 1008 1957
30. F. Freeman, and E.M. Karchetski J. Chem. Eng. Data 22 1977 355
31. J.A. Marshall, and P.G.M. Wuts J. Org. Chem. 42 1977 1794
32. G.A. Olah, and A.K. Mehrotra Synthesis 1982 962
33. T.S. Jin, G.Y. Du, Z.H. Zhang, and T.S. Li Synth. Commun. 27 1997 261
34. T.S. Li, Z.H. Zhang, and C.G. Fu Tetrahedron Lett. 38 1997 3285
35. B.M. Reddy, P.M. Sreekanth, and A. Kahn Synth. Commun. 34 2004 839
36. N. Deka, D.J. Kalita, R. Borah, and J.C. Sarma J. Org. Chem. 62 1997 563
37. J.M. Thomas Angew. Chem. Int. Ed. Engl. 27 1998 1673
38. N. Daka, R. Borah, D.J. Kalita, and J.C. Sarma J. Chem. Res. Synop. 1998 94
39. I. Scriabire Bull. Soc. Chim. Fr. 1961 1194
40. B.M. Trost, C.B. Lee, and J.M. Weiss J. Am. Chem. Soc. 117 1995 7247
41. C.D. Wang, and M.H. Li Synth. Commun. 32 2002 3469
42. T.S. Jin, G.Y. Du, and T.S. Li Indian J. Chem. Sect. B 37 1998 939
43. X.Y. Zhang, L.J. Li, and G.S. Zhang Green Chem. 5 2003 546
44. J.K. Michie, and J.A. Miller Synthesis 1981 824
45. J.S. Yadav, B.V.S. Reddy, and C. Srinivas Synth. Commun. 32 2002 1175
46. L. Yin, Z.-H. Zhang, Y.-M. Wang, and M.-L. Pang Synlett 2004 1727
47. B.F. Mirjalili, M.A. Zolfigol, A. Bamoniric, and N. Sheikhan J. Chin. Chem. Soc. 53 2006 955
48. M.M. Heravi, K. Bakhtiari, T. Benmorad, and H.A. Oskooie J. Chin. Chem. Soc. 54 2007 273
49. B.P. Bandgar, N.S. Joshi, and V.T. Kamble J. Chin. Chem. Soc. 54 2007 489
50. V.K. Aggarwal, S. Fonquerna, and G.P. Vennall Synlett 1998 849
51. K.L. Chandra, P. Saravanan, and V.K. Singh Synlett 2000 359
52. M.D. Carrigan, K.J. Eash, M.C. Oswald, and R.S. Mohan Tetrahedron Lett. 42 2001 8133
53. B. Karimi, and J. Maleki J. Org. Chem. 68 2003 4951
54. R. Ghosh, S. Maiti, A. Chakraborty, and R. Halder J. Mol. Catal. A: Chem. 215 2004 49
55. M.V. Joshi, and C.S. Narasimhan J. Catal 141 1993 308
56. D. Karmakar, D. Prajapati, and J.S. Sandhu J. Chem. Res. Synop. 1998 382
57. Z.H. Zhang, T.S. Li, and C.G. Fu J. Chem. Res. Synop. 1997 174
58. T.S. Li, Z.H. Zhang, and Y.J. Gao Synth. Commun. 28 1998 4665
59. T.S. Jin, Y.R. Ma, Z.H. Zhang, and T.S. Li Synth. Commun. 27 1997 3379
60. P. Kumar, V.R. Hedge, and T.P. Kumar Tetrahedron Lett. 36 1995 601
61. C. Pereira, B. Gigante, M.J. Marcelocurto, H. Carreyre, G. Perot, and M. Guisnet Synthesis 1995 1077
62. R. Ballini, M. Bordoni, G. Bosica, R. Maggi, and G. Sartori Tetrahedron Lett. 39 1998 7587
63. B. Karimi, H. Seradj, and G.R. Ebrahimian Synlett 2000 623
64. S.C. Roy, and B. Banerjee Synlett 2002 1677
65. T.S. Jin, G. Sun, Y.W. Li, and T.S. Li Green Chem. 4 2002 255
66. B. Karimi, G.R. Ebrahimian, and H. Seradj Synth. Commun. 32 2002 669
67. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, and K. Amani Tetrahedron Lett. 44 2003 3951
68. G.P. Romanelli, H.J. Thomas, G.T. Baronetti, and J.C. Autino Tetrahedron Lett. 44 2003 1301
69. M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, and M. Nocchetti Tetrahedron Lett. 43 2002 2709
70. G. Smitha, and C.S. Reddy Tetrahedron 59 2003 9571
71. N. Sumida, K. Nishioka, and T. Sato Synlett 2001 1921
72. J.S. Yadav, B.V.S. Reddy, C. Venugopal, and T. Ramalingam Synlett 2002 604
73. H.M.S. Kumar, B.V.S. Reddy, P.T. Reddy, and J.S. Yadav J. Chem. Res. Synop. 2000 86
74. B.C. Rana, J. Dutta, and A. Das Chem. Lett. 32 2003 366
75. A.K. Chakraborti, R. Thilagavathi, and R. Kumar Synthesis 2004 831
76. D.H. Aggen, J.N. Arnold, P.D. Hayes, N.J. Smoter, and R.S. Mohan Tetrahedron Lett. 60 2004 3675
77. A. Ziyaei, N. Azizi, and M.R. Saidi J. Mol. Catal. A: Chem. 238 2005 138
78. G.E. Negron, L.N. Palacios, D. Angeles, L. Lomas, and R. Gavino J. Braz. Chem. Soc. 16 3A 2005 490
79. 2: P. Ctelle, and J.P. Catteau Tetrahedron Lett. 33 1992 3855
80. 3: I. Mohammampoor-Baltork, and H. Aliyan J. Chem. Res. Synop. 1999 272
81. 3: I. Mohammampoor-Baltork, and H. Aliyan Synth. Commun. 29 1999 2741
82. 2O: I. Mohammampoor-Baltork, and H. Aliyan Indian J. Chem. Sect. B 38 1999 1223
83. 3H: T.S. Jin, G. Sun, Y.W. Li, and T.S. Li J. Chem. Res. Synop. 2003 30
84. 2O: H.Y. Niu, X.Y. Zhang, H.M. Guo, and J.J. Wang J. Chem. Res. Synop. 2004 764
85. 3: Z.H. Zhang, L. Yin, Y. Li, and Y.M. Wang Tetrahedron Lett. 46 2005 889
86. 2O: G.P. Romanelli, J.C. Autino, G. Baronetti, and H.J. Thomas Synth. Commun. 34 2004 3909
87. T.J. Mason, and J.P. Lorimer In Sonochemistry: Theory, Application and Uses of Ultrasound in Chemistry 1988 John Wiley and Sons New York
88. K.S. Suslick Ultrasound: It's Chemical, Physical and Biological Effects 1988 VCH Weinheim
89. A. Gaplovsky, M. Gaplovsky, S. Toma, and J. Luche J. Org. Chem. 65 2000 8444
90. R.R. Deshmukh, R. Rajagopal, and K.V. Srinivasan Chem. Commun. 2001 1544
91. F. Shirini, and N.G. Khaligh Phosphorus Sulfur Silicon Relat. Elem. 186 2011 2156
92. N.G. Khaligh J. Mol. Catal. A: Chem. 349 2011 63
93. N.G. Khaligh, and F. Shirini J. Mol. Catal. A: Chem. 348 2011 20
94. V. Calvino-Casilda, A.J. López-Peinado, R.M. Martín-Aranda, S. Ferrera- Escudero, and C.J. Durán-Valle Carbon 42 2004 1363
95. T.J. Mason, J.P. Lorimer, and B.P. Mistry Tetrahedron 41 1985 5201