Free accessResearch articleFirst published online 2007-7
Oxidative deprotection of tetrahydropyranyl and trimethylsilyl ethers in water using 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride under neutral conditions
A facile oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers in water using 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride as a new efficient reagent under neutral conditions is described. This methodology is ecofriendly and environmentally benign since it uses water as a solvent. In all reactions DABCO was regenerated, rechlorinated and reused several times.
(a) GreenT.W., and WutsP.G.M., Protective groups in organic synthesis, 3rd edn., John Wiley and Sons, New York, 1999, pp. 49; (b) P.J. Kocienski, In Protective groups; EndersD., NoyoriR., and TrostB.M., (eds.), Georg Thieme, Stuttgart, 1994, pp. 83; (c) P.J. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994, pp. 28; (d) A.J. Pearson and W.R. Roush, in Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups, Wiley, New York, 1999, pp. 84.
2.
(a) KrishnaveniN.S., SurendraK., ReddyM.A., NageswarY.V.D., and RaoK.R., J. Org. Chem., 2003, 68, 2018; (b) M.A. Reddy, K. Surendra, N. Bhanumathi and K.R. Rao, Tetrahedron, 2003, 58, 6003; (c) M.A. Reddy, N. Bhanumathi and K.R. Rao, Tetrahedron, 2002, 43, 3237; (d) M.A. Reddy, N. Bhanumathi and K.R. Rao, Synlett, 2000, 339; (e) A. Hajipour, S. Malakpour, I. Mohammadpoor-Baltork, M. Malakoutihah, Tetrahedron, 2002, 58, 143; (f) A. Khan, S. Islam, L.H. Choudhury and S. Ghosh, Tetrahedron Lett., 2004, 45, 9617.
3.
(a) SonnetP.E., Org. Prep. Proc. Int., 1978, 10, 91; (b) E.J.S. Parish, A. Kizito and R.W. Heidepriem, Synth. Commun., 1993, 23, 223; (c) I. Mohammadpoor-Baltork and P. Shirvani, Synthesis, 1997, 756; (d) I. Mohammadpoor-Baltork and B. Kharamsh, J. Chem. Res. (S), 1998, 146; (e) M. Lalonde and T.H. Chan, Synthesis, 1985, 817 and refs therein.
4.
(a) NarenderM., ReddyM.S., KumarP., NageswarY.V.D., and RaoK.R., Tetrahedron Lett., 2005, 46, 1971; (b) H. Tohama, T. Maegawa, S. Takizawa and Y. Kita, Adv. Synth. Catal., 2002, 344, 328.
5.
(a) HeraviM.M., TajbakhshM., Ghassemzadeh andM.Z. Naturforsch1999, 54B, 396; (b) M. Tajbakhsh, M.M. Heravi, S. Habibzadeh and M. Ghassemzadeh, J. Chem. Res. (s), 2001, 39; (c) M. Tajbakhsh, M.M. Heravi, S. Habibzadeh, Phosphorus, Sulfur, 2001, 176, 191; (d) M. Tajbakhsh, I. Moammadpoor-baltork and F. Ramzanian, J. Chem. Res. (S), 2001, 182; (e) M. Tajbakhsh, M.M. Heravi, S. Habibzadeh and M. Ghassemzadeh, Phosphorus, Sulfur, 2001, 176, 151; (f) M.M. Lakouraj, M. Tajbakhsh, V. Khojasteh and M.H. Golabi, Phosphorus, Sulfur, 2004, 179, 2645.
6.
(a) BlairL.K., BaldwinJ., and SmithW.C., J. Org. Chem., 1977, 42, 1816; (b) M.M. Heravi, F. Derikvand, M. Ghassemzadeh and B. Neumüller, Tetrahedron Lett., 2005, 46, 6243.
7.
TajbakhshM., HeraviM.M., and HabibzadehS., Synth. Commun., in press.
8.
TajbakhshM., and HabibzadehS., J. Chem. Res. (S), 2006, 539.
9.
(a) BanksR.E., BesheeshM.K., MohialdinS.N., and SharifI., J. Chem. Soc., Perkin Trans. 1, 1996, 2069; (b) J. Liu and C. Wong, Tetrahedron Lett., 2002, 43, 4037.
10.
(a) HeraviM.M., BehbahaniF.K., OskooieH.A., and Hekmat ShoarR., Tetrahedron Lett., 2005, 46, 2543; (b) A.T. Khan, E. Mondal, B.M. Borah and S. Ghosh, Eur. J. Org. Chem. 2003, 4113; (c) Y.S. Hon, C.F. Lee, R.J. Chen and P.H. Szu, Tetrahedron, 2001, 57, 5991; (d) Y.J. Kim and R.S. Varma, Tetrahedron Lett., 2005, 46, 1467; (e) B. Karimi, M. Khalkhali, J. Molecular Catalysis A: Chemical, 2005, 232, 113; (f) A.T. Khan, S. Ghosh and H.L. Choudhury, Eur. J. Org. Chem. 2005, 4891; (g) M.M. Mojtahedi, H. Abbasi and M.S. Abaee, J. Molecular Catalysis A: Chemical, 2006, 250, 6; (h) J.S. Yadav, B.V.S. Reddy, A.K. Basak, G. Baishya and A.V. Narsaiah, Synthesis, 2006, 3831.
11.
Aldrich Catalogue/Handbook of Fine Chemicals, 1992–1993.
12.
(a) MaityG., and RoyS.C., Synth. Commun., 1993, 23, 1667; (b) G. Neille, J. Org. Chem., 1960, 25, 1063.
