Deprotection and direct oxidative deprotection of trimethylsilyl ethers to their corresponding alcohols and carbonyl compounds with tris[trinitratocerium(IV)] paraperiodate, [(NO3)(3)Ce](3).H2IO6, in an aprotic solvent

被引：45

作者：

Firouzabadi, H

Shiriny, F

机构：

[1] Chemistry Department, Shiraz University

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 03期

关键词：

D O I：

10.1080/00397919608003633

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotection of structurally different trimethylsilyl ethers to their corresponding alcohols has been achieved in refluxing benzene in the presence of tris[trinitratocerium(IV)] paraperiodte in a few minutes. This reagent has also been used successfuly for the direct oxidation of trimethylsilyl ethers to their corresponding carbonyl compounds. Benzylic double bonds are prone to cleavage reactions with this method.

引用

页码：423 / 432

页数：10

共 22 条

[1] Deprotection and direct oxidative deprotection of trimethylsilyl ethers to their corresponding alcohols and carbonyl compounds with tris[trinitratocerium(IV)] paraperiodate, [(NO3)3Ce]3-H2IO6, in an aprotic solvent
Chemistry Department, Shiraz University, Shiraz 71454, Iran
Synth. Commun., 3 (423-432):
[2] Deprotection and Direct Oxidative Deprotection of Trimethylsilyl Ethers to Their Corresponding Alcohols and Carbonyl Compounds with tris[Trinitratocerium(IV)] Paraperiodate, [(NO3)3Ce]3.H2IO6, in an Aprotic Solvent
Synth Commun, 3 (423):
[3] (NO3)3CeBrO3:: Solvent-free oxidation of alcohols and deprotection and oxidative deprotection of trimethylsilyl ethers
Shirini, F
Esm-Hosseini, M
Hejazi, Z
SYNTHETIC COMMUNICATIONS, 2005, 35 (22) : 2913 - 2919
[4] TRIS[TRINITRATOCERIUM(IV)] PARAPERIODATE [(NO3)3CE]3H2IO6, AN EFFICIENT AND A VERSATILE OXIDANT IN ORGANIC-SYNTHESIS
FIROUZABADI, H
IRANPOOR, N
HAJIPOOR, G
TOOFAN, J
SYNTHETIC COMMUNICATIONS, 1984, 14 (11) : 1033 - 1042
[5] Bis[trinitratocerium (IV)] chromate [Ce(No3)2 Cro4] and tris-[trinitratocerium (IV)] paraperiodate [(No3)3Ce]3 H2IO6.: Two mild and efficient catalysts for tetrahydropyranylation of alcohols.
Oskooie, HA
Abaszadeh, MR
Zamani, FF
Heravi, MM
SYNTHETIC COMMUNICATIONS, 1998, 28 (12) : 2281 - 2285
[6] Direct oxidative deprotection of trimethylsilyl ethers to their corresponding carbonyl compounds with bis (trimethylsilyl) chromate supported onto silica gel in aprotic solvent.
Heravi, MM
Ajami, D
Tabar-Heydar, K
SYNTHETIC COMMUNICATIONS, 1999, 29 (06) : 1009 - 1012
[7] [Ce(NO3)3]3•H2IO6:: Efficient oxidation reactions under solvent-free conditions
Shirini, F
Esm-Hosseini, M
Hejazi, Z
Mohammadpoor-Baltork, I
JOURNAL OF CHEMICAL RESEARCH, 2006, (01) : 29 - 31
[8] Fe(NO3)3•9H2O/Fe(HSO4)3:: An efficient reagent system for the oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers in the absence of solvent
Shirini, Farhad
Zolfigol, Mohammad A.
Abri, Abdol-Reza
ARKIVOC, 2008, : 14 - 18
[9] Oxidative deprotection of trimethylsilyl ethers to carbonyl compounds with PdCl2(PhCn)2-CrO3 and clay-bis(trimethylsilyl) chromate in solventless system
Heravi, MM
Ajami, D
Aghapoor, K
Ghassemzadeh, M
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 158 : 151 - 156
[10] Aluminum chloride (AlCl3) promotes selective oxidative deprotection of benzylic trimethylsilyl and tert-butyldimethylsilyl ethers to the corresponding carbonyl compounds with manganese dioxide (MnO2)
Firouzabadi, H
Etemadi, S
Karimi, B
Jarrahpour, AA
SYNTHETIC COMMUNICATIONS, 1999, 29 (24) : 4333 - 4339

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