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
Free accessResearch articleFirst published online May, 2007
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
The 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. The 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, p. 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, p. 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 and 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, P. Shirvani, Synthesis, 1997, 756; (d) I. Mohammadpoor-Baltork, B. Kharamsh, J. Chem. Res. (S), 1998, 146; (e) M. Lalonde, T.H. Chan, Synthesis, 1985, 817 and references cited 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., and GhassemzadehM., 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 and 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 and 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.
13.
AndersonE.L., CaseyJ.E., GreeneL.C., LaffertyJ.J., and ReiffH.E., J. Med. Chem., 1964, 7, 259.
14.
VanV.T., and VieheH.G., Angew. Chem (Int Ed), 1974, 86, 45.
15.
WorrallD.E., J. Am. Chem. Soc., 1937, 59, 933.
16.
KatrizkyA.R., WangM., ZhangS., VoronkovM.V., and SteelP.J., J. Org. Chem., 2001, 44, 6787.
17.
AchofieldK., GrimmettM.R., and KeeneB.R.T., Amination and substituted amination in azoles in Heteroaromatic Nitrogen Compounds: The Azoles.Cambridge Univ. Press, Eds. New York, 1976, pp133 and references therein.
18.
SinghO.M., IlaH., and JunjappaH., J. Chem. Soc. Perkin Trans. 1, 1997, 3561.
19.
BarunO., IlaH., JunjappaH., and SinghO.M., J. Org. Chem., 2000, 65, 1583.
20.
(a) ChauhanS.M.S., and JunjappaH., Synthesis, 1975, 798. (b) J.N. Viswakarma, B.K.R. Chowdhury, H. Ila and H. Junjappa, Indian J. Chem., 1985, 24B, 472.
21.
GrotjahnD.B., VanS., CombsD., LevD.A., SchneiderC., RideoutM., MeyerC., HernadezG., and MejoradoL., J. Org. Chem., 2002, 67, 9200.
