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Volumn 1996, Issue 1, 1996, Pages 69-71

A Mild and Efficient Method for the Cleavage of tert-Butyldimethylsilyl and Tetrahydropyranyl Ethers by Ceric Ammonium Nitrate in Methanol

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EID: 0008307168     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5320     Document Type: Article
Times cited : (75)

References (40)
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    • For some more methods for cleavage of TBDMS ethers, see: (a). Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295. (b). Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35. (c). Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234. (d). Dahlhoft, W. V.; Taba, K. M. Synthesis 1986, 561. (e.). Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
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    • Kelly, D.R.1    Roberts, S.M.2    Newton, R.F.3
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    • For some more methods for cleavage of TBDMS ethers, see: (a). Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295. (b). Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35. (c). Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234. (d). Dahlhoft, W. V.; Taba, K. M. Synthesis 1986, 561. (e.). Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 35
    • Metcalf, B.W.1    Burkhart, J.P.2    Jund, K.3
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    • For some more methods for cleavage of TBDMS ethers, see: (a). Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295. (b). Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35. (c). Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234. (d). Dahlhoft, W. V.; Taba, K. M. Synthesis 1986, 561. (e.). Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
    • (1980) Synthesis , pp. 234
    • Batten, R.J.1    Dixon, A.J.2    Taylor, R.J.K.3    Newton, R.F.4
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    • For some more methods for cleavage of TBDMS ethers, see: (a). Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295. (b). Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35. (c). Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234. (d). Dahlhoft, W. V.; Taba, K. M. Synthesis 1986, 561. (e.). Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
    • (1986) Synthesis , pp. 561
    • Dahlhoft, W.V.1    Taba, K.M.2
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    • For some more methods for cleavage of TBDMS ethers, see: (a). Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295. (b). Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35. (c). Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980, 234. (d). Dahlhoft, W. V.; Taba, K. M. Synthesis 1986, 561. (e.). Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1669
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    • and references cited therein
    • For literature methods for deprotection of THP ethers, see: Raina, S.; Singh, V. K. Synth. Commun. 1995, 25, 2395 and references cited therein.
    • (1995) Synth. Commun. , vol.25 , pp. 2395
    • Raina, S.1    Singh, V.K.2
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    • Cerium (IV) Oxidation of Organic Compounds
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    • (1986) Organic Syntheses by Oxidation with Metal Compounds , pp. 569-631
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    • (1992) Tetrahedron Lett. , vol.33 , pp. 2777
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    • (a). Review: Ho, T.-L.: Cerium (IV) Oxidation of Organic Compounds. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; deJonge, C. R. H. I. Eds.; Plenum Press: New York, 1986, pp. 569-631. (b). Magnus, P.; Barth, L. Tetrahedron Lett. 1992, 33, 2777. (c). Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786. (d). Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, 3707. (e). Wilson, S. R.; Augelli-szafran, C. E. Tetrahedron 1988, 44, 3983.
    • (1990) J. Org. Chem. , vol.55 , pp. 4786
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    • (a). Review: Ho, T.-L.: Cerium (IV) Oxidation of Organic Compounds. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; deJonge, C. R. H. I. Eds.; Plenum Press: New York, 1986, pp. 569-631. (b). Magnus, P.; Barth, L. Tetrahedron Lett. 1992, 33, 2777. (c). Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786. (d). Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, 3707. (e). Wilson, S. R.; Augelli-szafran, C. E. Tetrahedron 1988, 44, 3983.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3707
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  • 27
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    • (a). Review: Ho, T.-L.: Cerium (IV) Oxidation of Organic Compounds. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; deJonge, C. R. H. I. Eds.; Plenum Press: New York, 1986, pp. 569-631. (b). Magnus, P.; Barth, L. Tetrahedron Lett. 1992, 33, 2777. (c). Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786. (d). Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, 3707. (e). Wilson, S. R.; Augelli-szafran, C. E. Tetrahedron 1988, 44, 3983.
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    • note
    • The pH of CAN solution in methanol at 0°C indicates that the solution is acidic (mild). After few hours (usually 5-6 h) the colour of the solution turns colourless (pH 1-2).


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