SciELO - Scientific Electronic Library Online

 
vol.64Highly efficient method for solvent-free synthesis of diarylmethane and triarylmethane from benzylic alcohols using P2O5/Al2O3 or P2O5/SiO2 at room temperatureSpeciation of Co(II), Ni(II) and Cu(II) complexes with L-glutamic acid in Dioxan-Water mixtures índice de autoresíndice de materiabúsqueda de artículos
Home Pagelista alfabética de revistas  

Servicios Personalizados

Articulo

Indicadores

Links relacionados

  • En proceso de indezaciónCitado por Google
  • En proceso de indezaciónSimilares en Google

Compartir


South African Journal of Chemistry

versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350

S.Afr.j.chem. (Online) vol.64  Durban  2011

 

RESEARCH ARTICLE

 

[H2-cryptand 222]2+(Br3-)2 as a tribromide-type catalyst for the trimethylsilylation/tetrahydropyranylation of alcohols

 

 

Gholamabbas ChehardoliI, *; Mohammad Ali ZolfigolII; Vahid KhakyzadehII; Hadi GholamiKII; Khodabakhsh NiknamIII

ISchool of Pharmacy, Hamedan University of Medical Sciences, 65178 Hamedan, Iran
IIFaculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran
IIIDepartment of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

 

 


ABSTRACT

A stable organic tribromide, [H2-cryptand 222]2+(Br3-)2 was utilized as an active catalyst for the trimethylsilylation/ tetrahydropyranylation of alcohols. The method is general for the preparation of OH-protected aliphatic (acyclic and cyclic), aromatic, primary, secondary and tertiary alcohols.

Keywords: [H2-cryptand 222]2+(Br3-)2, trimethylsilylation, tetrahydropyranylation, alcohols, tribromide, TMS-ether, THP-ether


 

 

Full text available only in pdf format.

 

Acknowledgements

This paper was extracted from the M.Sc. thesis of Vahid Khakyzadeh. The authors acknowledge financial support for this work from the research affairs of Hamedan University of Medi-calSciences,Hamedan,I.R. Iranandpartialsupportofthis work by the Research Affairs Office of Bu-Ali Sina University (Grant number 32-1716 entitled development of chemical methods, reagent and molecules.),and also Center ofExcellence inDevelopment of Chemical Method (CEDCM) Hamedan, I.R. Iran.

 

References

1 (a) Z.B. Huang and S.H. Chang, Synlett., 2005, 1703;         [ Links ] (b) Z.B. Huang and S.H. Chang, Synlett., 2005, 2257;         [ Links ] (c) Z.B. Huang, T.J. Kang and S.H. Chang, Tetrahedron Lett., 2005, 46,3461;         [ Links ] (d) Z.B. Huang, S.H. Kim and S.H. Chang,Synlett.,2006,1707;         [ Links ] (e) Z.B. Huangand S.H. Chang, Tetrahedron Lett., 2005, 46, 5351.         [ Links ]

2 (a) L.F. Lindoy, J. Iran. Chem. Soc., 2004, 1, 1;         [ Links ] (b) J. Hua and Y.G. Wang, 2005, Chem. Lett., 34, 1.         [ Links ]

3 C. Muthukumar and S.D. Kesarkar andD.N. Srivastava, J. Electroanal. Chem., 2007, 602, 172.         [ Links ]

4 (a) H.J. Bushmann, G. Wenz, E. Schollmeyer and L. Mutihac, Inorg. Chem. Commun., 2001, 4, 211;         [ Links ] (b) T.M. Letcher, J.D. Mercer-Chalmers and R.L. Kay, Pure & Appl. Chem., 1994, 66, 419;         [ Links ] (c) M. Dhifet, M.S. Belkhiria, J. Daran and H. Nasri, Acta Cryst., 2009, E65, m967.         [ Links ]

5 H.R. Pouretedal and A. Semnani, Iran. J. Chem. Chem. Eng., 2005, 24, 53.         [ Links ]

6 V.J. Mathew and S.M. Khopkar, J. Radioanal. Nucl. Chem. Lett., 1995, 201, 281.         [ Links ]

7 G.Bracke,M.SatirandP.Krau,Clays and Clay Minerals,1995, 43, 732.         [ Links ]

8 M.N. Gandhi and S.M. Khopkar, Mikrochim. Acta, 1993, 111, 93.         [ Links ]

9 (a) F.D. Cattaway and G. Hoyle, J. Chem. Soc., 1923, 654;         [ Links ] (b) M. Avramoff, J. Weiss and O. Schaechter, J. Org. Chem., 1963, 28, 3256.         [ Links ]

10 S. Kajigneshi, T. Kakinami, H. Tokiyama, T. Hirakawa and T. Okamoto,Chem. Lett.,1987, 627.         [ Links ]

11 R.E.Buckles, A.I.Popov, W.F.Zeleznyand R.J.Smith, J.Am.Chem.Soc., 1951, 73, 4525.         [ Links ]

12 H.A. Muathen, J. Org. Chem., 1992, 57, 2740.         [ Links ]

13 L.F. Fieser and M. Fieser, Reagents for Organic Synthesis, Wiley, New York, USA, 1967.         [ Links ]

14 I. Yavari and A. Shaabani,J.Chem.Res.(S), 1994, 7, 274.         [ Links ]

15 M.M. Heravi, F. Derikvand, M. Ghassemzadeh and B. Neumuller, Tetrahedron Lett., 2005, 46, 6243.         [ Links ]

16 W. Bao and Z. Wang,GreenChem., 2006, 8, 1028.         [ Links ]

17 C. Chiappe, E. Leandri and D. Pieraccini, Chem. Commun., 2004, 2536.         [ Links ]

18 M.A. Zolfigol, G. Chehardoli, S. Salehzadeh, H. Adams and M.D. Ward,Tetrahedron Lett.,2007,48, 7969.         [ Links ]

19 (a)M.K.Chaudhuri,A.T.KhanandB.K.Patel,TetrahedronLett.,1998, 39, 8163;         [ Links ] (b) H.Z. Boeini, J. Iran. Chem. Soc., 2009, 6, 547.         [ Links ]

20 T.W. GreenandP.G.M. Wuts,Protective Groups in Organic Synthesis,3rd edn., Wiley, New York, USA, 1999.         [ Links ]

21 (a) W.H. Pinnick, B.S. Bal and N.H. Lajis, Tetrahedron Lett., 1978, 4261;         [ Links ] (b)T.Morita,Y.Okomoto and H.Sakuti,Tetrahedron Lett., 1980, 21,835;         [ Links ] (c) J. Cossy and P. Pale, Tetrahedron Lett., 1978, 6093;         [ Links ] (d) S. Tarkelson and C. Anisworth, Synthesis, 1976, 722.         [ Links ]

22 C.A. Bruynes and T.K. Jurrines, J. Org. Chem., 1982, 47, 3966.         [ Links ]

23 (a) Z.H. Zhang, T.S. Li, F. Yang and C.G. Fu, Synth. Commun., 1998,28, 305;         [ Links ] (b) M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati and U. Constantino, Synth. Commun., 1999, 29, 541;         [ Links ] (c) H. Firouzabadi, N. Iranpoor, K. Amani and F. Nowrouzi, J. Chem. Soc, Perkin Trans. 1, 2002, 2601;         [ Links ] (d) B. Karimi and B. Golshani, J. Org. Chem., 65, 2000, 7228;         [ Links ] (e) A. Khazaei, M.A. Zolfigol, A. Rostami and A.G. Choghamarani, Catal. Commun., 2006, 7, 399;         [ Links ] (f) F. Shirini, M.A. Zolfigol and K. Mohammadi, Phosphorous, Sulfur Silicon Relat. Elem., 2003, 178, 1567;         [ Links ] (g) F. Shirini, M.A. Zolfigol and M. Abedini, Bull. Chem. Soc. Jpn., 2005, 78, 1982;         [ Links ] (h) A. Khazaei, S. Rahmati and A. Rostami, Helv. Chim. Acta, 2009, 92, 1434;         [ Links ] (i) A. Khazaei, M.A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam and J. Saien, Catal. Commun., 8, 2007, 917;         [ Links ] (j) M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S. Chahardahcheric and Z. Tavakoli, J. Organomet. Chem., 2008, 693, 2041;         [ Links ] (k) M. Mojtahedi, H. Abbasi and M.S. Abaee, J. Mol. Catal. A: Chem., 2006, 250, 6.         [ Links ]

24 T. Mineno, Tetrahedron Lett, 43, 2002, 7975.         [ Links ]

25 (a) R.G. Jones and M.J. Mann, J. Am. Chem. Soc, 1953, 75, 4048;         [ Links ] (b) M. Miyashita, A. Yoshikoshi and P.A. Grieco, J. Org. Chem., 1977, 42, 3772;         [ Links ] (c) Y. Ogawa and M. Shibasaki, Tetrahedron Lett., 1984, 25, 663;         [ Links ] (d) V.V. Namboodiri and R.S. Varma, Tetrahedron Lett., 2002, 43, 1143;         [ Links ] (e) N. Ravindranath, C. Ramesh and B. Das, Synlett, 2001, 1777;         [ Links ] (f) N. Rezai, F.A. Meybodi and P. Salehi, Synth. Commun., 2000, 30, 1799;         [ Links ] (g) B. Karimi and M. Khalkhali, J. Mol. Catal. A: Chem., 2005, 232, 113;         [ Links ] (h) Y. Wang, X. Wu and Z. Jiang, Tetrahedron Lett., 2004, 45, 2973;         [ Links ] (i) M.M. Heravi, F.K. Behbahani, H.A. Oskooie and R.H. Shoar, TetrahedronLett., 2005, 46, 2543;         [ Links ] (j) S. Naik, R. Gopinath andB.K. Patel, Tetrahedron Lett., 2001, 42, 7679;         [ Links ] (k) A. Khazaei, A. Rostami and M. Mahboubifar, Catal. Commun., 2007, 8, 383.         [ Links ]

26 (a) M.A. Zolfigol, M.H. Zebarjadian, G. Chehardoli, H. Keypour, S. Salehzadeh and M. Shamsipur, J. Org. Chem., 2001, 66, 3619;         [ Links ] (b) M.A. Zolfigol, M.H. Zebarjadian, G. Chehardoli, S.E. Mallakpour and M. Shamsipur, Tetrahedron, 2001, 57, 1627;         [ Links ] (c) K. Niknam and M.A. Zolfigol, J. Iran. Chem. Soc., 2006, 3, 59.         [ Links ]

27 (a) M.A. Zolfigol, G. Chehardoli, E. Ghaemi, E. Madrakian, R. Zare, T. Azadbakht, K. Niknam and S. Mallakpour, Monatsh. Chem., 2008 139, 261;         [ Links ] (b) M.A. Zolfigola, E. Kolvari, N. Koukabi, S. Salehzadeh, G. Chehardoli, I.S. Tidmarsh and K. Niknam, J. Iran. Chem. Soc., 2011, 8, 484;         [ Links ] (c) G. Chehardoli, M.A. Zolfigol, V. Khakyzadeh, R. Golbedaghi, N.A. Hall and A.G. Blackman, J. Chin. Chem. Soc., 2011, 58, in press.         [ Links ]

28 (a) R. Ghorbani-Vaghei, M.A. Zolfigol, M. Chegeny and H. Veisi, Tetrahedron Lett., 2006, 47, 4505;         [ Links ] (b) K. Niknam, M.A. Zolfigol, G. Chehardoli and M. Dehghanian, Chin. J. Catal., 2008, 29, 901;         [ Links ] (c) M.A. Zolfigol, G. Chehardoli, M. Dehghanian, K. Niknam, F. Shirini and A. Khoramabadi-Zad, J. Chin. Chem. Soc., 2008, 55, 885;         [ Links ] (d) K. Niknam, M.A. Zolfigol, D. Saberi and M. Khonbazi, Chin. J. Chem., 2009, 27, 1548;         [ Links ] (e) F. Shirini, M.A. Zolfigol and M. Abedini, Monatsh. Chem., 2009, 140, 61.         [ Links ]

29 The room-temperature crystal structure of [H2-cryptand 222]2+(Br3-)2 has recently been reported. See A.N. Chekhlov, J. Struct. Chem., 2007, 48, 137.         [ Links ]

 

 

Received 16 May 2011
Revised 8 July 2011
Accepted 21 July 2011

 

 

* To who correspondence should be addressed. E-mail: chehardoli@umsha.ac.ir; cheh1002@gmail.com

Creative Commons License Todo el contenido de esta revista, excepto dónde está identificado, está bajo una Licencia Creative Commons