How to cite this paper
Zeynizadeh, B & Sorkhabi, S. (2020). Highly efficient method for oximation of aldehydes in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides.Current Chemistry Letters, 9(3), 121-130.
Refrences
1. Roman, G., Comanita, E. & Comanita, B. (2002) Synthesis and reactivity of Mannich bases. Part 15: Synthesis of 3-(2-(1-pyrazolyl)ethyl)-1,2-benzisoxazoles. Tetrahedron 58, 1617‒1622.
2. Xu, X., Henninger, T., Abbanat, D., Bush, K., Foleno, B., Hilliard, J. & Macielag, M. (2005) Synthesis and antibacterial activity of C2-fluoro, C6-carbamate ketolides, and their C9-oximes. Bioorg. Med. Chem. Lett. 15, 883‒887
3. Gopalakrishnan, M., Thanusu J., & Kanagarajan, V. (2009) A facile solid-state synthesis and in vitro antimicrobial activities of some 2,6-diarylpiperidin/tetrahydrothiopyran and tetrahydropyran-4-one oximes. J. Enzyme Inhib. Med. Chem. 24, 669‒675.
4. Li, J. T., Li, X. L. & Li, T. S. (2006) Synthesis of oximes under ultrasound irradiation. Ultras. Sonochem. 13, 200‒202.
5. Ren, R. X. & Ou. W. (2001) Preparation of cyclic ketoximes using aqueous hydroxylamine in ionic liquids. Tetrahedron Lett. 42, 8445‒8446.
6. Beckman, E. (1890) Chem. Ber. 23, 1680.
7. Beckman, E. (1909) Lieb. Ann. Chem. 365, 200.
8. Zeynizadeh, B. & Karimkoshteh, M. (2013) Magnetic Fe3O4 nanoparticles as recovery catalyst for preparation of oximes under solvent-free condition. J. Nanostruct. Chem. 3, 57‒64.
9. Ramanjaneyulu, K., Rao, P. S., Rambabu, T., Jayarao, K., Devi, C. B. T. & Rao, B. V. (2012) Cupper supported silica promoted one-pot synthesis of aromatic oxime derivatives. Der Pharma Chemica 4, 473‒478.
10. Bo, R. K, Gi, H. S, Jeum, J. K, Yong, J. Y. (2013) A development of rapid, practical and selective process for preparation of Z-oximes. J Korean Chem. Soc. 57, 295–299.
11. Setamdideh, D., Khezri, B. & Esmaeilzadeh, S. (2012) Synthesis of oximes with NH2OH·HCl/ DOWEX 50WX4 system. J. Chin. Chem. Soc. 59, 1119–1124.
12. Zaho, S. Huang, L. & Song, Y. F. (2013) Highly selective and efficient Lewis acid–base catalysts based on lanthanide-containing polyoxometalates for oximation of aldehydes and ketones. Eur. J. Inorg. Chem. 2013, 1659‒1663.
13. Fazaeli, R., Tangestaninejad, S. & Aliyan, H. (2007) Solvent-free selective oximation of aldehydes using facile and reusable heterogeneous polyoxometalate. Catal. Commun. 8, 205‒210.
14. Osadchenko, I. M. & Tomilov, A. P. (2002) Phase-transfer catalysis in synthesis of oximes. Russ. J. Appl. Chem. 75, 511–512.
15. Zang, H., Wang, M., Cheng, B. W. & Song, J. (2009) Ultrasound-promoted synthesis of oximes catalyzed by a basic ionic liquid [bmim]OH. Ultrason. Sonochem. 16, 301‒303.
16. Mantegazza, M. A., Cesana, A. & Pastori, M. (1996) Ammoximation of Ketones on titanium silicalite. Chem. Ind. 68, 97‒106.
17. Tvaruzkova, Z., Habersberger, K., Zilkovo, N. & Jiru, P. (1991) Role of surface complexes on titanium-silicate in the ammoximation of cyclohexanone with hydrogen peroxide. Appl. Catal. 79, 105‒114.
18. Pertrini, G., Leofanti, G., Mantegazza, M. A. & Pignataro, F. (1996) Caprolactam via ammoximation. ACS Symp. Ser. 626, 33‒48.
19. La Bars, J., Dakka, J. & Sheldon, R. A. (1996) Ammoximation of cyclohexanone and hydroxyaromatic ketones over titanium molecular sieves. Appl. Catal. 36, 69‒80.
20. Armor, J. N. (1980) Ammoximation: direct synthesis of oximes from ammonia, oxygen and ketones. J. Am. Chem. Soc. 102, 1453‒1454.
21. Raja, R., Sankar, G. & Thomas, N. M. (2001) Bifunctional molecular sieve catalysts for the benign ammoximation of cyclohexanone: one-step, solvent-free production of oxime and ε-caprolactam with a mixture of air and ammonia. J. Am. Chem. Soc. 123, 8153‒8154.
22. Kad, G. L., Bhandari, M., Kaur, J., Rathee, R. & Singh, J. (2001) Solventless preparation of oximes in the solid state and via microwave irradiation. Green Chem. 3, 275‒277.
23. Hajipour, A. R., Mallakpour, S. E. & Imanzadeh, G. (1999) A rapid and convenient synthesis of oximes in dry media under microwave irradiation. J. Chem. Res. 228‒229.
24. Bandgar, B. P., Sadavarte, V. S., Uppalla, L. S. & Govande, R. (2001) Chemoselective preparation of oximes, semicarbazones, and tosylhydrazones without catalyst and solvent. Monat. Chem. 132, 403‒406.
25. Sharghi, H. & Sarvari, M. H. (2000) A mild and versatile method for the preparation of oximes by use of calcium oxide. J. Chem. Res. 24‒25.
26. Guo, J. J., Jin, T. S., Zhang, S. L. & Li, T. S. (2001) TiO2/SO42−: an efficient and convenient catalyst for preparation of aromatic oximes. Green Chem. 3, 193‒195.
27. Xia, J. J. & Wang, G. W. (2007) Efficient preparation of aldoximes from arylaldehydes, ethylenediamine and oxone in water. Molecules 12, 231‒236.
28. Li, J. T., Li, X. L., Li, T. S. (2006) Synthesis of oximes under ultrasound irradiation. Ultrason. Sonochem. 13, 200‒202.
29. Zeynizadeh, B. & Amjadi, E. (2009) Facile oximation of carbonyl compounds with titanyl acetylacetonate/NH2OH system. Asian J. Chem. 21, 3611‒3616.
30. Lakhinath, S., Baruah, J. M. & Thakur, A. J. (2011) A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry. Org. Med. Chem. Lett. 1, 12.
31. Yip, A. C. K. & Hu, X. (2009) Catalytic activity of clay-based titanium silicalite-1 composite in cyclohexanone ammoximation. Ind. Eng. Chem. Res. 48, 8441–8450.
32. Moghadam, M., Tangestaninejad, S., Mirkhani, V., Mohammadpoor-Baltork, I. & Moosavifar, M. (2009) Host (nanocavity of dealuminated zeolite Y)–guest (12-molybdophosphoric acid) nanocomposite material: an efficient and reusable catalyst for oximation of aldehydes. Appl. Catal. A Gen. 358, 157–163.
33. Gentili, P. & Pedetti, S. (2012) A remarkably simple α-oximation of aldehydes via organo-SOMO catalysis. Chem. Commun. 48, 5358–5360.
34. Sloboda-Rozner, D. & Neumann, R. (2006) Aqueous biphasic catalysis with polyoxometalates: oximation of ketones and aldehydes with aqueous ammonia and hydrogen peroxide. Green Chem. 8, 679–681.
35. Special issue on polyoxometalates (1998) Chem. Rev. 98, 1–390.
36. Neumann, R. (1998) Polyoxometalate complexes in organic oxidation chemistry. Prog. Inorg. Chem. 47, 317–370.
37. Kozhevnikov, I. V. (2002) Catalysis by Polyoxometalates. Volume 2, Wiley, Chichester.
38. Long, D. L., Tsunashima, R. & Cronin, L. (2010) Polyoxometallate als Bausteine für funktionelle nanosysteme. Angew. Chem. 122, 1780–1802.
39. Zhao, S., Liu, L. & Song, Y. F. (2012) Highly selective oximation of aldehydes by reusable heterogeneous sandwich-type polyoxometalate catalyst. Dalton Trans. 41, 9855–9858.
40. Xing, S., Han, Q., Shi, Z., Wang, S., Yang, P., Wu, Q. & Li, M. (2017) A hydrophilic inorganic framework based on a sandwich polyoxometalate: unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine. Dalton Trans. 46, 11537–11541.
41. Zeynizadeh, B. & Sorkhabi, S. (2016) Fast and efficient protocol for solvent-free reduction of nitro compounds to amines with NaBH4 in the presence of bis-thiourea complexes of bivalent cobalt nickel, copper and zinc chlorides. J. Chem. Soc. Pak. 38, 679–684.
42. Zeynizadeh, B. & Sorkhabi, S. (2018) Fast and efficient method for silylation of alcohols and phenols with HMDS in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides. Phosphorus, Sulfur, Silicon Relat. Elem. 193, 127‒135.
43. Parmar, S., Kumar, Y. & Mittal, A. (2010) Synthesis, spectroscopic and pharmacological studies of bivalent copper, zinc and mercury complexes of thiourea. South Afr. J. Chem. 63, 123–129.
44. https://en.wikipedia.org/wiki/Irving–Williams_series (accessed on Nov. 14, 2019).
45. Irving, H. M. N. H. & Williams, R. J. P. (1953) The stability of transition-metal complexes. J. Chem. Soc. 3192–3210.
46. Rappoport, Z. (1966) CRC Handbook of Tables for Organic Compound Identification, 3rd ed., Boca Raton.
47. Smolikova, J., Exner, O., Barbaro, G., Macciantelli, D. & Dondoni, A. (1980) Configuration and conformation of acyl derivatives of hydroxylamine. Part 22. Hydroxamoyl chlorides. A revision. J. Chem. Soc. Perkin Trans. II, 1051‒1056.
48. Brehm, L. & Watson. J. (1972) The crystal structure of syn-p-nitrobenzaldoxime. Acta Cryst. B 28, 3646‒3652.
49. Daltons, R. & Foley, H. G. (1973) O-carbamoyl oximes. J. Org. Chem. 38, 4200‒4203.
2. Xu, X., Henninger, T., Abbanat, D., Bush, K., Foleno, B., Hilliard, J. & Macielag, M. (2005) Synthesis and antibacterial activity of C2-fluoro, C6-carbamate ketolides, and their C9-oximes. Bioorg. Med. Chem. Lett. 15, 883‒887
3. Gopalakrishnan, M., Thanusu J., & Kanagarajan, V. (2009) A facile solid-state synthesis and in vitro antimicrobial activities of some 2,6-diarylpiperidin/tetrahydrothiopyran and tetrahydropyran-4-one oximes. J. Enzyme Inhib. Med. Chem. 24, 669‒675.
4. Li, J. T., Li, X. L. & Li, T. S. (2006) Synthesis of oximes under ultrasound irradiation. Ultras. Sonochem. 13, 200‒202.
5. Ren, R. X. & Ou. W. (2001) Preparation of cyclic ketoximes using aqueous hydroxylamine in ionic liquids. Tetrahedron Lett. 42, 8445‒8446.
6. Beckman, E. (1890) Chem. Ber. 23, 1680.
7. Beckman, E. (1909) Lieb. Ann. Chem. 365, 200.
8. Zeynizadeh, B. & Karimkoshteh, M. (2013) Magnetic Fe3O4 nanoparticles as recovery catalyst for preparation of oximes under solvent-free condition. J. Nanostruct. Chem. 3, 57‒64.
9. Ramanjaneyulu, K., Rao, P. S., Rambabu, T., Jayarao, K., Devi, C. B. T. & Rao, B. V. (2012) Cupper supported silica promoted one-pot synthesis of aromatic oxime derivatives. Der Pharma Chemica 4, 473‒478.
10. Bo, R. K, Gi, H. S, Jeum, J. K, Yong, J. Y. (2013) A development of rapid, practical and selective process for preparation of Z-oximes. J Korean Chem. Soc. 57, 295–299.
11. Setamdideh, D., Khezri, B. & Esmaeilzadeh, S. (2012) Synthesis of oximes with NH2OH·HCl/ DOWEX 50WX4 system. J. Chin. Chem. Soc. 59, 1119–1124.
12. Zaho, S. Huang, L. & Song, Y. F. (2013) Highly selective and efficient Lewis acid–base catalysts based on lanthanide-containing polyoxometalates for oximation of aldehydes and ketones. Eur. J. Inorg. Chem. 2013, 1659‒1663.
13. Fazaeli, R., Tangestaninejad, S. & Aliyan, H. (2007) Solvent-free selective oximation of aldehydes using facile and reusable heterogeneous polyoxometalate. Catal. Commun. 8, 205‒210.
14. Osadchenko, I. M. & Tomilov, A. P. (2002) Phase-transfer catalysis in synthesis of oximes. Russ. J. Appl. Chem. 75, 511–512.
15. Zang, H., Wang, M., Cheng, B. W. & Song, J. (2009) Ultrasound-promoted synthesis of oximes catalyzed by a basic ionic liquid [bmim]OH. Ultrason. Sonochem. 16, 301‒303.
16. Mantegazza, M. A., Cesana, A. & Pastori, M. (1996) Ammoximation of Ketones on titanium silicalite. Chem. Ind. 68, 97‒106.
17. Tvaruzkova, Z., Habersberger, K., Zilkovo, N. & Jiru, P. (1991) Role of surface complexes on titanium-silicate in the ammoximation of cyclohexanone with hydrogen peroxide. Appl. Catal. 79, 105‒114.
18. Pertrini, G., Leofanti, G., Mantegazza, M. A. & Pignataro, F. (1996) Caprolactam via ammoximation. ACS Symp. Ser. 626, 33‒48.
19. La Bars, J., Dakka, J. & Sheldon, R. A. (1996) Ammoximation of cyclohexanone and hydroxyaromatic ketones over titanium molecular sieves. Appl. Catal. 36, 69‒80.
20. Armor, J. N. (1980) Ammoximation: direct synthesis of oximes from ammonia, oxygen and ketones. J. Am. Chem. Soc. 102, 1453‒1454.
21. Raja, R., Sankar, G. & Thomas, N. M. (2001) Bifunctional molecular sieve catalysts for the benign ammoximation of cyclohexanone: one-step, solvent-free production of oxime and ε-caprolactam with a mixture of air and ammonia. J. Am. Chem. Soc. 123, 8153‒8154.
22. Kad, G. L., Bhandari, M., Kaur, J., Rathee, R. & Singh, J. (2001) Solventless preparation of oximes in the solid state and via microwave irradiation. Green Chem. 3, 275‒277.
23. Hajipour, A. R., Mallakpour, S. E. & Imanzadeh, G. (1999) A rapid and convenient synthesis of oximes in dry media under microwave irradiation. J. Chem. Res. 228‒229.
24. Bandgar, B. P., Sadavarte, V. S., Uppalla, L. S. & Govande, R. (2001) Chemoselective preparation of oximes, semicarbazones, and tosylhydrazones without catalyst and solvent. Monat. Chem. 132, 403‒406.
25. Sharghi, H. & Sarvari, M. H. (2000) A mild and versatile method for the preparation of oximes by use of calcium oxide. J. Chem. Res. 24‒25.
26. Guo, J. J., Jin, T. S., Zhang, S. L. & Li, T. S. (2001) TiO2/SO42−: an efficient and convenient catalyst for preparation of aromatic oximes. Green Chem. 3, 193‒195.
27. Xia, J. J. & Wang, G. W. (2007) Efficient preparation of aldoximes from arylaldehydes, ethylenediamine and oxone in water. Molecules 12, 231‒236.
28. Li, J. T., Li, X. L., Li, T. S. (2006) Synthesis of oximes under ultrasound irradiation. Ultrason. Sonochem. 13, 200‒202.
29. Zeynizadeh, B. & Amjadi, E. (2009) Facile oximation of carbonyl compounds with titanyl acetylacetonate/NH2OH system. Asian J. Chem. 21, 3611‒3616.
30. Lakhinath, S., Baruah, J. M. & Thakur, A. J. (2011) A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry. Org. Med. Chem. Lett. 1, 12.
31. Yip, A. C. K. & Hu, X. (2009) Catalytic activity of clay-based titanium silicalite-1 composite in cyclohexanone ammoximation. Ind. Eng. Chem. Res. 48, 8441–8450.
32. Moghadam, M., Tangestaninejad, S., Mirkhani, V., Mohammadpoor-Baltork, I. & Moosavifar, M. (2009) Host (nanocavity of dealuminated zeolite Y)–guest (12-molybdophosphoric acid) nanocomposite material: an efficient and reusable catalyst for oximation of aldehydes. Appl. Catal. A Gen. 358, 157–163.
33. Gentili, P. & Pedetti, S. (2012) A remarkably simple α-oximation of aldehydes via organo-SOMO catalysis. Chem. Commun. 48, 5358–5360.
34. Sloboda-Rozner, D. & Neumann, R. (2006) Aqueous biphasic catalysis with polyoxometalates: oximation of ketones and aldehydes with aqueous ammonia and hydrogen peroxide. Green Chem. 8, 679–681.
35. Special issue on polyoxometalates (1998) Chem. Rev. 98, 1–390.
36. Neumann, R. (1998) Polyoxometalate complexes in organic oxidation chemistry. Prog. Inorg. Chem. 47, 317–370.
37. Kozhevnikov, I. V. (2002) Catalysis by Polyoxometalates. Volume 2, Wiley, Chichester.
38. Long, D. L., Tsunashima, R. & Cronin, L. (2010) Polyoxometallate als Bausteine für funktionelle nanosysteme. Angew. Chem. 122, 1780–1802.
39. Zhao, S., Liu, L. & Song, Y. F. (2012) Highly selective oximation of aldehydes by reusable heterogeneous sandwich-type polyoxometalate catalyst. Dalton Trans. 41, 9855–9858.
40. Xing, S., Han, Q., Shi, Z., Wang, S., Yang, P., Wu, Q. & Li, M. (2017) A hydrophilic inorganic framework based on a sandwich polyoxometalate: unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine. Dalton Trans. 46, 11537–11541.
41. Zeynizadeh, B. & Sorkhabi, S. (2016) Fast and efficient protocol for solvent-free reduction of nitro compounds to amines with NaBH4 in the presence of bis-thiourea complexes of bivalent cobalt nickel, copper and zinc chlorides. J. Chem. Soc. Pak. 38, 679–684.
42. Zeynizadeh, B. & Sorkhabi, S. (2018) Fast and efficient method for silylation of alcohols and phenols with HMDS in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides. Phosphorus, Sulfur, Silicon Relat. Elem. 193, 127‒135.
43. Parmar, S., Kumar, Y. & Mittal, A. (2010) Synthesis, spectroscopic and pharmacological studies of bivalent copper, zinc and mercury complexes of thiourea. South Afr. J. Chem. 63, 123–129.
44. https://en.wikipedia.org/wiki/Irving–Williams_series (accessed on Nov. 14, 2019).
45. Irving, H. M. N. H. & Williams, R. J. P. (1953) The stability of transition-metal complexes. J. Chem. Soc. 3192–3210.
46. Rappoport, Z. (1966) CRC Handbook of Tables for Organic Compound Identification, 3rd ed., Boca Raton.
47. Smolikova, J., Exner, O., Barbaro, G., Macciantelli, D. & Dondoni, A. (1980) Configuration and conformation of acyl derivatives of hydroxylamine. Part 22. Hydroxamoyl chlorides. A revision. J. Chem. Soc. Perkin Trans. II, 1051‒1056.
48. Brehm, L. & Watson. J. (1972) The crystal structure of syn-p-nitrobenzaldoxime. Acta Cryst. B 28, 3646‒3652.
49. Daltons, R. & Foley, H. G. (1973) O-carbamoyl oximes. J. Org. Chem. 38, 4200‒4203.