Abstract
Reaction of 18-crown-6 with KI in ethanol solution followed by addition of iodine (I2) afforded a unique triiodide salt with a nanotube-like structure ({[K.18-Crown-6]I3}n). It is shown that this reagent may be used for the chemoselective trimethylsilylation of alcohols. The synthesis of the crystalline reagent is a good example of crystal engineering. Reagent was recycled and reused.
Similar content being viewed by others
References
G.W. Gokel, W.M. Leevy, M.E. Weber, Chem. Rev. 104 (2004) 2723.
Z.B. Huang, S.H. Chang, Synlett (2005) 1703.
Z.B. Huang, S.H. Chang, Synlett (2005) 2257.
Z.B. Huang, T.J. Kang, S.H. Chang, Tetrahedron Lett. 46 (2005) 3461.
Z.B. Huang, S.H. Kim, S.H. Chang, Synlett (2006) 1707.
Z.B. Huang, S.H. Chang, Tetrahedron Lett. 46 (2005) 5351.
Z.B. Huang, S.H. Kim, S.H. Chang, Bull. Korean Chem. Soc. 27 (2006) 893.
Z.B. Huang, S.H. Chang, J. Inclus. Phenomen. Marocycl. Chem. (2006) 341.
Z.B. Huang, T.J. Kang, S.H. Chang, New. J. Chem. 29 (2005) 1616.
J.C.W. Gray, K. Barry, E.J. Lindberg, T.A. Houston, Tetrahedron Lett. 48 (2007) 2683.
L.F. Lindoy, J. Iran. Chem. Soc. 1 (2004) 1.
J. Hua, Y.G. Wang, Chem. Lett. 34 (2005) 98.
R.M. Izatt, K. Pawlak, J.S. Bradshaw, Chem. Rev. 91 (1991) 1721.
R.M. Izatt, J.S. Bradshaw, S.A. Nielsen, J.D. Lamb, J.J. Christensen, Chem. Rev. 85 (1985) 271.
D. Braga, M. Polito, E. Dichiaranti, K. Rubini, F. Grepioni, Chem. Commun. (2007) 1594.
D. Pasini, M. Ricci, Curr. Org. Chem. 4 (2007) 59.
J.W. Steed, E. Sakellariou, P.C. Junk, M.K. Smith, Chem. Eur. J. 7 (2001) 1240.
V.V. Ponomarova, K.V. Domasevitch, Crystal Engineering 5 (2002) 137.
Y. Luo, H. Liu, F. Xi, L. Li, X. Jin, C.C. Han, C. Chan, J. Am. Chem. Soc. 125 (2003) 6014.
Y. Cui, S.J. Lee, W. Lin, J. Am. Chem. Soc. 125 (2003 6447.
I. Tornieporthoetting, T. Kalapotke, Ang. Chem. It. Ed. Eng. 29 (1990) 677.
D.J. Tudela, Chem. Edu. 79 (2002) 558.
A.J. Blake, R.O. Gould, S. Parsons, C. Radek, M. Schroder, Acta Crystallogr. Sect. C-Cryst. Struct. Commun. 52 (1996) 24.
C. Walbaum, I. Pantenburg, G. Meyer, Z. Anorg. Allg. Chem. 633 (2007) 1609.
A.N. Chekhlov, Russ. J. Coord. Chem. 30 (2004) 8.
C. Runschke, G. Meyer, Z. Anorg. Allg. Chem. 623 (1997) 1493.
A.K. Nurtaeva, G. Hu, E.M. Holt, Acta Crystallogr. Sect. C-Cryst. Struct. Commun. 54 (1998) 594.
K.F. Tebbe, M. Elessawi, S.A. Elkhalik, Z. Anorg. Allg. Chem. 50 (1995) 1429.
I. Pantenburg, I. Muller, Acta Crystallogr. Sect. C-Cryst. Struct. Commun. 59 (2003) M 427.
I. Pantenburg, K. Tebbe, Z. Anorg. Allg. Chem. 628 (2002) 1780.
L. Kloo, P.H. Svensson, M.J. Taylor, J. Chem. Soc. Dalton Trans. (2000) 1066.
C.C. Hines, C.B. Bauer, R.D. Rogers, New J. Chem. 31 (2007) 762.
P.H. Svensson, L. Kloo, Chem. Rev. 103 (2003) 1649, and references cited therein.
H. Chown, P.A.W. Dean, D.C. Craig, N.T. Lucas, M.L. Scudder, New J. Chem. 27 (2003) 704.
M.A. Zolfigol, A. Ghorbani-Choghamarani, H. Hazarkhani, Synlett (2002) 1002.
M.A. Zolfigol, A. Bamoniri, Synlett (2002) 1621.
M.A. Zolfigol, D. Habibi, B.F. Mirjalili, A. Bamoniri, Tetrahedron Lett. 44 (2003) 3345.
M.A. Zolfigol, K. Niknam, F. Nazari, J. Chin. Chem. Soc. 53 (2006) 669.
K. Niknam, M.A. Zolfigol, J. Iran. Chem. Soc. 3 (2006) 59.
M.A. Zolfigol, M.H. Zebarjadian, G. Chehardoli, H. Keypour, S. Salehzadeh, M. Shamsipur, J. Org. Chem. 66 (2001) 3619.
M.A. Zolfigol, M.H. Zebarjadian, G. Chehardoli, S.E. Mallakpour, M. Shamsipur, Tetrahedron 57 (2001) 1627.
M.A. Zolfigol, M.H. Zebarjadian, M.M. Sadeghi, I. Mohammadpoor-Baltork, H.R. Memarian, M. Shamsipur, Synth. Commun. 31 (2001) 929.
M.A. Zolfigol, M.H. Zebarjadian, I. Mohammadpoor-Baltork, M. Shamsipur, Synth. Commun. 32 (2002) 2803.
M.A. Zolfigol, G. Chehardoli, S. Salehzadeh, H. Adams, M.D. Ward, Tetrahedron Lett. 48 (2007) 7969.
M. Sievert, V. Krenzel, H.Z. Bock, Kristallogr. 211 (1996) 794.
T.W. Green, P.G.M. Wuts, Protective Groups in Organic Synthesis, 3th ed., Wiley, New York, 1999.
G. Van Look, G. Simchen, J. Heberle, Silylating Agents, 2th ed., Fluka, Buches, Switzerland, 1995.
M.A. Zolfigol, I. Mohammadpoor-Baltork, D. Habibi, B.F. Mirjalili, A. Bamoniri, Tetrahedron Lett. 44 (2003) 8165.
See: http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=heartcut.
E.J. Corey, B.B. Sinder, J. Am. Chem. Soc. 94 (1972) 2549.
G.A. Olah, B.G.B. Gupta, S.C. Narang, R. Malhotra, J. Org. Chem. 44 (1979) 4272.
B.A.D. Sa, D. McLeod, J.G. Verkade, J. Org. Chem. 62 (1997) 5057.
M. Lalonde, T.H. Chan, Synthesis (1985) 817.
P. Gauttret, S. El-Ghamarti, A. Legrand, D. Coutrier, B. Rigo, Synth. Commun. 26 (1996) 707.
F. Shirini, M.A. Zolfigol, K. Mohammadi, Phosphorus Sulfur, and Silicon 178 (2003) 1567.
H. Firouzabadi, A.R. Sardarian, Z. Khayat, B. Karimi, S. Tangestaninejad, Synth. Commun. 27 (1997) 2709.
M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, U. Constantino, Synth. Commun. 29 (1999) 541.
N. Azizi, R. Yousefi, M.R. Saidi, J. Organomet. Chem. 691 (2006) 817.
Z.H. Zhang, T.S. Li, F. Yang, C.G. Fu, Synth. Commun. 28 (1998) 3105.
V.H. Tillu, V.H. Jadhav, H.B. Borate, R.D. Wakharkar, Arkivoc (2004) 83.
H. Firouzabadi, N. Iranpoor, K. Amani, F. Nowrouzi, J. Chem. Soc., Perkin Trans. 1 (2002) 2601.
R. Ghorbani-Vaghei, M.A. Zolfigol, M. Chegeny, H. Veisi, Tetrahedron Lett. 47 (2006) 4505.
B. Akhlaghinia, S. Tavakoli, Synthesis (2005) 1775.
M.M. Mojtahedi, H. Abbasi, M.S. Abaee, J. Mol. Catal. A: Chem. 250 (2006) 6.
B. Karimi, B. Golshani, J. Org. Chem. 65 (2000) 7228.
F. Shirini, M.A. Zolfigol, M. Abedini, Bull. Chem. Soc. Jpn. 78 (2005) 1982.
F. Shirini, E. Mollarazi, Synth. Commun. 36 (2006) 1109.
H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Ghassamipour, Synthesis (2005) 595.
H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Ghassamipour, J. Organomet. Chem. 689 (2004) 3197.
H.R. Shaterian, F. Shahrekipoor, M. Ghashang, J. Mol. Catal. A: Chem. 272 (2007) 142.
D. Zareyee, B. Karimi, Tetrahedron Lett. 48 (2007) 1277.
A. Khazaei, M.A, Zolfigol, A. Rostami, A. Ghorbani Choghamarani, Catal. Commun. 8 (2007) 543.
A. Khazaei, M.A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam, J. Saien, Catal. Commun. 8 (2007) 917.
M.A. Zolfigol, F. Shirini, G. Chehardoli, E. Kolvari, J. Mol. Catal. A: Chem. 265 (2006) 271.
M.A. Zolfigol, F. Shirini, A.G. Choghamarani, Synthesis 12 (2006) 2043.
M.A. Zolfigol, M. Bagherzadeh, S. Mallakpour, G. Chehardoli, A. Ghorbani-Choghamarani, N. Koukabi, M. Dehghanian, M. Doroudgar, J. Mol. Catal. A: Chem. 270 (2007) 219.
P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh, Curr. Org. Chem. 10 (2006) 2171.
E. Kolvari, A. Ghorbani-Chghamarani, P. Salehi, F. Shirini, M.A. Zolfigol, J. Iran. Chem. Soc. 4 (2007) 126.
F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Curr. Org. Chem. 12 (2008) 183.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zolfigol, M.A., Kolvari, E., Koukabi, N. et al. A new crystal engineering approach for the synthesis of {[K.18-Crown-6]I3}n as a nanotube-Like and recyclable catalyst for the chemoselective silylation of alcohols. JICS 8, 484–494 (2011). https://doi.org/10.1007/BF03249082
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF03249082