(NO3)3CeBrO3: Solvent-free oxidation of alcohols and deprotection and oxidative deprotection of trimethylsilyl ethers

Synthetic Communications

Volumn 35, Issue 22, 2005, Pages 2913-2919

  Shirini, Farhad ^a   Esm Hosseini, Majid ^b   Hejazi, Zoha ^a,b  

^a UNIVERSITY OF GUILAN   (Iran)

^b URMIA UNIVERSITY   (Iran)

Author keywords

Alcohols; Deprotection; Oxidation; Solvent free conditions; Trinitratocerium (IV) bromate

Indexed keywords

ALCOHOL DERIVATIVE; BROMATE; ETHER DERIVATIVE; SOLVENT; TRIMETHYLSILYL DERIVATIVE; TRINITRATOCERIUM BROMATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION TIME;

EID: 29144445974     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500297362     Document Type: Article

References (18)

1. 6: As a veratile and efficient reagent for cleavage of carbon ⇌ nitrogen double bonds under heterogeneous and non-aqueous conditions. Synth. Commun. 2001, 31, 3775.
2. Al-Haq, N.; Sullivan, A. C.; Wilson, R. H. Oxidation of alcohols using cerium(IV) alkyl phosphonate modified silica. Tetrahedron Lett. 2003, 44, 769.
3. Laali, K. K.; Herbert, M.; Cushnyr, B.; Bahatt, A.; Terrano, D. Benzylic oxidation of aromatics with cerium(IV) triflate; synthetic scope and mechanistic insight. J. Chem. Soc., Perkin Trans. 2001, 1, 578.
4. Imamoto, T.; Koide, Y.; Hiayama, S. Cerium(IV) trifluoromethanesulfonate as a strong oxidizing agent. Chem. Lett. 1990, 1445.
5. Iranpoor, N.; Mohammadpoor-Baltork, I.; Shirini, F. Cerric ammonium nitrate, as an efficient catalyst for mild and selective opening of epoxides in the presence of water, thiols and acetic acid. Tetrahedron 1991, 47, 9861.
6. Iranpoor, N.; Shirini, F. Tris[trinitrato Ce(IV)]paraperiodate, as an efficient heterogeneous catalyst for alcoholysis, acetolysis, and hydrolysis of epoxides. Synth. Commun. 1994, 24, 1959.
7. 4. Synth. Commun. 1998, 28, 347.
8. Iranpoor, N.; Shekarriz, M. Homocoupling of substituted benzenes to symmetrical biaryls with mercury(II) in the presence of cerium(IV). J. Chem. Res., Synop. 1999, 442.
9. 3. Synth. Commun. 2001, 31, 767.
10. Akbar, A. Guilan University: Iran, 2000, M.Sc. Thesis.
11. Shirini, F.; Zolfigol, M. A.; Pourhabib, A. Efficient cleavage of carbon-nitrogen double bonds under solvent-free conditions. Synth. Commun. 2002, 32, 2837.
12. 2. J. Chem. Res., Synop. 2003, 1, 28.
13. Shirini, F.; Zolfigol, M. A.; Mohammadi, K. Silica sulfuric acid as a mild and efficient reagent for the acetylation of alcohols in solution and under solvent-free conditions. Bull. Korean Chem. Soc. 2004, 25, 325.
14. 2O in the oxidation of trimethylsilyl ethers. Synth. Commun. 1996, 26, 649.
15. Hajipour, A. R.; Mallakpour, S. E.; Mahammadpoor-Baltork, I.; Malakoutikhah, M. 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. 2002, 58, 143.
16. Karimi, B.; Golshani, B. Mild and highly efficient method for the silylation of alcohols using hexamethyldisilazane catalyzed by iodine under nearly neutral reaction conditions. J. Org. Chem. 2000, 65, 7228.
17. Firouzabadi, H.; Karimi, B. Zinc chloride-catalyzed silylation of alcohols and phenols by hexamethyldisilazane. A highly chemoselective reaction. Synth. Commun. 1993, 23, 1633.
18. Shirini, F.; Zolfigol, M. A.; Mohammadi, K. A mild and efficient method for chemoselective silylation of alcohols using hexamethyldisilazane in the presence of silica chloride. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 1567.