Mild and Efficient Method for Oxidative Deprotection of Trimethylsilyl Ethers Mediated by Tetraethylammonium Superoxide

References

• Greene , T. W. and Wuts , P. G. M. 1991 . Protective Groups in Organic Synthesis , 2nd edn. New York : Wiley‐Interscience .
   Google Scholar
• Kocienski , P. J. 1994 . Protecting Groups New York : Thieme .
   Google Scholar
• Muzart , J. 1993 . Silyl ethers as protecting groups for alcohols: Oxidative deprotection and stability under alcohol oxidation condition . Synthesis , : 11 – 27 .
   Web of Science ®Google Scholar
• Muzart , J. and N'Ait , A. A. 1991 . Bis(triphenylsilyl) chromate catalyzed oxidation of silyl ethers by tert‐butyl hydroperoxide . Synlett , : 497 – 498 .
   Web of Science ®Google Scholar
• Firouzabadi , H. and Mohammadpoor‐Baltork , I. 1994 . Lewis acid promoted reaction (IV), oxidation deprotection of trimethylsilyl ethers with silver and sodium bromates; AgBrO3, NaBrO3 . Synth. Commun. , 24 : 1065
   Web of Science ®Google Scholar
• Mohammadpoor‐Baltork , I. and Pouranshirvani , S. 1997 . 3‐Carboxypyridium chlorochromate (CPCC): A mild, efficient and inexpensive reagent for oxidative deprotection of trimethylsilyl and tetrahydropyranyl ether under non‐aqueous conditions . Synthesis , : 756 – 758 .
   Web of Science ®Google Scholar
• Heravi , M. M. , Ajami , D. and Ghassemzadeh , M. 1999 . Wet alumina supported chromium (VI) oxide: A mild, efficient and inexpensive reagent for oxidative deprotection of trimethylsilyl and tetrahydropyranyl ether in a solventless system . Synthesis , : 393 – 394 .
   Web of Science ®Google Scholar
• Hajipour , A. R. , Mallakpour , S. E. , Mohammadpoor‐Baltork , I. and Malakoutikhah , M. 2002 . Benzyltriphenylphosphonium chlorate (BTPPC) as a new and mild reagent for oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers of benzylic alcohols under non‐aqueous conditions . Tetrahedron , 58 : 143 – 145 .
   Web of Science ®Google Scholar
• Jin , T.‐S. , Li , Y.‐W. , Sun , G. , Song , X.‐R. and Li , T.‐S. 2003 . Phosphomolybdic acid, an efficient and practical reagent for the oxidative deprotection of trimethylsilyl ethers with silver and sodium bromates . J. Chem. Res. , : 322 – 323 .
   Web of Science ®Google Scholar
• Iranpoor , N. , Firouzabadi , H. and Pourali , A. R. 2005 . Selective oxidation of benzylic alcohols and ethers and oxidative cleavage of benzylic tetrahydropyranyl and trimethylsilyl ethers to their carbonyl compounds by dinitrogen tetraoxide–impregnated activated charcoals (N2O4/Charcoal) . Synth. Commun. , 35 ( 11 ) : 1527 – 1533 .
   Web of Science ®Google Scholar
• Hajipour , A. R. , Bagheri , H. R. and Ruoho , A. E. 2005 . An efficient method for selective deprotection of trimethylsilyl ethers and tetrahydropyranyl ethers under solvent‐free conditions . Bull. Korean Chem. Soc. , 26 ( 11 ) : 1689 – 1691 .
   Web of Science ®Google Scholar
• Singh , S. , Verma , M. and Singh , K. N. 2004 . Superoxide induced oxidation of γ‐lactones to γ‐ketocarboxylic acids in aprotic medium . Synth. Commun. , 34 ( 24 ) : 4471 – 4475 .
   Web of Science ®Google Scholar
• Singh , S. and Singh , K. N. 2005 . Superoxide‐mediated synthesis of N‐aminoaziridines from N‐aminoheterocycles and olefins . Synth. Commun. , 35 ( 19 ) : 2597 – 2602 .
   Web of Science ®Google Scholar
• Shukla , A. K. , Verma , M. and Singh , K. N. 2004 . Superoxide induced deprotection of 1,3‐dithiolanes: A convenient method of dedithioacetalization . Indian J. Chem. , 43B : 1748 – 1752 .
   Google Scholar
• Singh , K. N. and Kumar , R. 2005 . Some studies on the reaction of in situ generated tetraethylammonium superoxide with 2‐oxazolin‐5‐ones . Indian J. Chem. , 44B : 381 – 386 .
   Google Scholar
• Neville , G. 1960 . Synthesis of 4‐(2,3‐epoxypropoxy)phenyltrimethylsilane . J. Org. Chem. , 25 : 1063 – 1065 .
   Web of Science ®Google Scholar