Skip to main content
SpringerLink
Log in

Copper(II) complexes with 18-membered decaaza macrocycles: synthesis, characterization and catalytic activity

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

New square-planar copper(II) complexes of 18-membered decaaza macrocyclic ligands: 5,6,14,15-tetramethyl-1,3,4,7,8,10,12,13,16,17-decaazacyclooctadecane (Me4[18]aneN10); 1,10-dimethyl-(Me2Me4[18]aneN10); 1,10-diethyl-(Et2Me4[18]aneN10); 1,10-dipropyl-(Pr2Me4[18]aneN10); 1,10-dibutyliso-(Bu2Me4[18]aneN10) and 1,10-dibenzyl-5,6,14,15-tetramethyl-1,3,4,7,8,10,12,13,16,17-decaazacylooctadecane [(Benzyl)2Me4[18]aneN10)] have been prepared by a one-pot template condensation of formaldehyde and 2,3-butanedihydrazone with alkyl and benzylamine in the presence of copper(II) ion. The complexes of the decaaza macrocycle have been characterized by elemental analyses, i.r., u.v.–vis., conductometric and magnetic measurements. The spectra of [Cu(R2Me4[18]ane N10)](ClO4)2shows that the four nitrogen (α-diimine) atoms are coordinated to the copper(II) ion. These complexes are found to be effective catalysts for the selective oxidation of tetrahydrofuran to yield the corresponding tetrahydrofuran-2-one and a small amount of tetrahydrofuran-2-ol and 4-hydroxybutyraldehyde, using diluted H2O2 as the oxidant.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J.B. Harrowfield A.J. Herbit P.A. Lay A.M. Sargeson A.M. Bond (1983) J. Am. Chem. Soc. 105 5503 Occurrence Handle10.1021/ja00354a067 Occurrence Handle1:CAS:528:DyaL3sXks1ehsbg%3D

    Article  CAS  Google Scholar 

  2. (a) S.G. Kang , M.S. Kim and K. Ryu, Polyhedron 15, 1835 (1996); (b) B. Korybut-Daszkiewicz, J. Coord. Chem., 19, 101 (1988); (c) R.W. Hay, M.P. Pujari, B. Korybut-Dasz-Kiewicz, G. Ferguson and B. Ruhl, J. Chem. Soc., Dalton Trans., 85 (1989); (d) B. Korybut-Daszkiewicz, J. Chem. Soc., Dalton Trans., 1673 (1992).

  3. M. Rossignoli, P.V. Bernhardt, G.A. Lawrance and M. Maeder, Aust. J. Chem., 50, 529 (1997) and ref. therein.

  4. (a) I. Murase, I. Ueda, N. Marubayashi, S. Kida, N. Matsumoto, M. Kudo, M. Toyohara, K. Hiate and M. Mikuriya, J. Chem. Soc., Dalton Trans., 2763 (1990); (b) E. Asato, S. Kida and I. Murase, Inorg. Chem, 61, 2666 (1989).

  5. K.P. Wainwright, Coord. Chem. Rev, 166, 35 (1997) and ref. therein.

  6. G.A. Lawrence and M.A. O’Leary, Polyhedron, 6, 1291 (1987); M.P. Suh, W. Shin, D. Kim and S. Kim, Inorg. Chem., 23, 618 (1984); M.P. Suh, D. Kim and S. Kim, Inorg. Chem., 24, 3712 (1985); M.P. Suh, W. Shin, H. Kim and C.H. Koo, Inorg. Chem., 26, 1846 (1987); M.P. Suh and S.-G. Kang, Inorg. Chem., 27, 2544 (1988); M.P. Suh, W. Shin, S. -G. Kang, M.S. Lah and T. -M. Chung, Inorg. Chem., 28, 1602 (1989); S.-K. Jung, S.-G. Kang and M.P. Suh, Bull. Kor. Chem Soc., 10, 362(1989); M.P. Suh, S.-G. Kang, V.L. Goedken, and S.-H. Park, Inorg. Chem., 30, 365(1991); M.P. Suh and D. Kim, Inorg. Chem., 24, 3712 (1985); M.P. Suh, W. Shin, H. Kim and C.H. Koo, Inorg. Chem., 26, 1846 (1987).

  7. G. Pattrick, M.P. Ngwenya, S.M. Dobson and R.D. Hancock, J. Chem. Soc. Dalton Trans., 1295 (1991).

  8. (a) R.D. Hancock, Acc. Chem. Res., 23, 253 (1990); (b) R.D. Hancock, S.M. Dobson, A. Evers, P.W. Wade, M.P. Ngwenya, J.C.A. Boeyens and K.P. Wainwright, J. Am. Chem. Soc., 110, 2788 (1988); (c) R.D. Hancock, M.P. Ngwenya, P.W. Wade, J.C.A. Boeyens and S.M. Dobson, Inorg. Chim. Acta, 164, 73 (1989).

  9. (a) P. Comba, N.F. Curtis, G.A. Lawrence, M.A. O’Leary, B.W. Skelton and A.H. White, J. Chem. Soc., Dalton Trans., 2145 (1988); (b) P. Comba, N.F. Curtis, G.A. Lawrence, A.M. Sargeson, B.W. Skelton and A.H. White, Inorg. Chem., 25, 4260 (1986); (c) P. Comba, N.F. Curtis, G.A. Lawrence, M.A. O’Leary, B.W. Skelton and A.H. White, J. Chem. Soc., Dalton Trans., 497 (1988).

  10. M. Salavati-Niasari M. Rezai-Adaryani (2004) Polyhedron 23 1325 Occurrence Handle10.1016/j.poly.2004.02.016 Occurrence Handle1:CAS:528:DC%2BD2cXjs1eku70%3D

    Article  CAS  Google Scholar 

  11. M. Salavati-Niasari H. Najafian (2003) Polyhedron 22 263 Occurrence Handle10.1016/S0277-5387(03)00342-5

    Article  Google Scholar 

  12. M. Salavati-Niasari (2004) Inorg. Chem. Comm. 7 698 Occurrence Handle10.1016/j.inoche.2004.01.010 Occurrence Handle1:CAS:528:DC%2BD2cXjvVantL0%3D

    Article  CAS  Google Scholar 

  13. D.D. Perrin W.L.F. Armarego D.R. Perrin (1980) Purification of Laboratory Chemicals Pergamon, Headington Hill Hall Oxford, London, England

    Google Scholar 

  14. D.H. Bush J.C. Bailar (1956) J. Am. Chem. Soc. 78 1137 Occurrence Handle10.1021/ja01587a014

    Article  Google Scholar 

  15. A. Anichini F. Fabbrizzi F. Paoletti (1977) Inorg. Chem. Acta 24 L21 Occurrence Handle10.1016/S0020-1693(00)93812-X Occurrence Handle1:CAS:528:DyaE2sXlslKrtrc%3D

    Article  CAS  Google Scholar 

  16. G. Patrick, M.P. Ngwenya, S.M. Dobson and R.D. Hancock, J.␣Chem. Soc., Dalton Trans., 1295 (1991).

  17. C.L. Hill (Ed.), Activation and Functionalization of Alkanes, Wiley, 1989.

  18. C.A. Godfrey, in B.M. Trost and I. Fleming, (eds.),Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, vol. 7, p. 235; P. Muller, in S. Patai,ed. The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues, Wiley, New York, 1980, Suppl. E, p. 469.

  19. I.T. Harrison and S. Harrison, J. Chem. Soc. Chem. Commun., 752 (1966).

  20. L.M. Berkowitz P.N. Rylander (1958) J. Am. Chem. Soc. 80 6682 Occurrence Handle10.1021/ja01557a053 Occurrence Handle1:CAS:528:DyaG1MXpsVahtQ%3D%3D

    Article  CAS  Google Scholar 

  21. P.H.J. Carlsen T. Katsuki V.S. Martin K.B. Sharpless (1981) J. Org. Chem. 46 3936 Occurrence Handle10.1021/jo00332a045 Occurrence Handle1:CAS:528:DyaL3MXltFChsro%3D

    Article  CAS  Google Scholar 

  22. M. Sommorigo and H. Alper, J. Mol. Catal. A: Chem., 88, 151 (1994) and ref. therein.

  23. A.K. Mandal V. Khanna J. Iqbal (1996) Tetrahedron Lett. 37 3769 Occurrence Handle10.1016/0040-4039(96)00678-8 Occurrence Handle1:CAS:528:DyaK28Xjtlemu7k%3D

    Article  CAS  Google Scholar 

  24. M. Sasidharan S. Suresh A. Sudalaj (1995) Tetrahedron Lett. 36 9071 Occurrence Handle10.1016/0040-4039(95)01937-D Occurrence Handle1:CAS:528:DyaK2MXpslyjt70%3D

    Article  CAS  Google Scholar 

  25. M. Salavati-Niasari F. Farzaneh M. Ghandi (2001) J. Mol. Catal. A. Chem. 175 105 Occurrence Handle10.1016/S1381-1169(01)00101-7

    Article  Google Scholar 

  26. M. Salavati-Niasari (2004) J. Mol. Catal. A: Chem 217 87 Occurrence Handle10.1016/j.molcata.2004.02.022 Occurrence Handle1:CAS:528:DC%2BD2cXksVertrc%3D

    Article  CAS  Google Scholar 

  27. M. Salavati-Niasari H. Banitaba (2003) J. Mol. Catal. A: Chem 201 43 Occurrence Handle10.1016/S1381-1169(03)00128-6 Occurrence Handle1:CAS:528:DC%2BD3sXkt1WksL4%3D

    Article  CAS  Google Scholar 

  28. M. Salavati-Niasari J. Hasanalian H. Najafian (2004) J. Mol. Catal A: Chem. 209 204

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, Iran

    Masoud Salavati-Niasari, Mostafa Rezai-Adaryani & Samansa Heydarzadeh

Authors
  1. Masoud Salavati-Niasari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mostafa Rezai-Adaryani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Samansa Heydarzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Salavati-Niasari, M., Rezai-Adaryani, M. & Heydarzadeh, S. Copper(II) complexes with 18-membered decaaza macrocycles: synthesis, characterization and catalytic activity. Transition Met Chem 30, 445–450 (2005). https://doi.org/10.1007/s11243-005-1017-2

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-005-1017-2

Keywords

Search

Navigation