Efficient and selective oxidative deprotection of tetrahydropyranyl ethers, ethylene acetals and ketals with silver and sodium bromates in the presence of aluminum chloride

被引：0

作者：

Mohammadpoor-Baltork, I ^{[1
]}

Nourozi, AR ^{[1
]}

机构：

[1] Esfahan Univ, Dept Chem, Esfahan 81744, Iran

来源：

SYNTHESIS-STUTTGART | 1999年 / 03期

关键词：

tetrahydropyranyl ethers; acetals; ketals; oxidative deprotection; bromates;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Primary and secondary tetrahydropyranyl (THP) ethers are efficiently transformed to their carbonyl compounds with AgBrO3 and NaBrO3/AlCl3. Ethylene acetals and ketals are transformed to their carboxylic acids and ketones respectively with AgBrO3/AlCl3 in refluxing acetonitrile. AgBrO3/AlCl3 is also able to transform ethylene acetals to aldehydes in refluxing carbon tetrachloride in high yields. In refluxing acetonitrile, ethylene acetals and ketals are transformed to aldehydes and ketones with NaBrO3/AlCl3 We have also found that tetrahydropyranyl ethers are oxidized selectively in the presence of ethylene acetals and ketals with these reagents.

引用

页码：487 / 490

页数：4

共 11 条

[1] An efficient method for selective deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers, ethylene acetals, and ketals under microwave irradiation
Hajipour, AR
Mallakpour, SE
Mohammadpoor-Baltork, I
Khoee, S
SYNTHETIC COMMUNICATIONS, 2002, 32 (04) : 611 - 620
[2] An efficient method for selective deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers, ethylene acetals and ketals under solvent-free conditions
Hajipour, AR
Mallakpour, SE
Mohammadpoor-Baltork, I
Khoee, S
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2002, 41 (06): : 1251 - 1256
[3] Selective, convenient and efficient deprotection of trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals with oxone under non-aqueous conditions
Mohammadpoor-Baltork, I
Amini, MK
Farshidipoor, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (12) : 2775 - 2778
[4] Selective, convenient and efficient deprotection of trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals with oxone under non-aqueous conditions
1600, Chemical Soc of Japan, Tokyo, Japan (73):
[5] Oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers and ethylene acetals with benzyltriphenylphosphonium peroxomonosulfate in the presence of bismuth chloride under non-aqueous conditions
Hajipour, AR
Mallakpour, SE
Mohammadpoor-Baltork, I
Adibi, H
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 165 : 155 - 163
[6] Oxidative deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers, and ethylene acetals with benzyltriphenylphosphonium peroxymonosulfate under microwave irradiation
Hajipour, AR
Mallakpour, SE
Baltork, IM
Adibi, H
SYNTHETIC COMMUNICATIONS, 2001, 31 (11) : 1625 - 1631
[7] Benzyltriphenylphosphonium peroxodisulfate: a mild and inexpensive reagent for selective oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals under non-aqueous and aprotic conditions
Tajbakhsh, M
Mohammadpoor-Baltork, I
Ramzanian-Lehmali, F
JOURNAL OF CHEMICAL RESEARCH, 2001, (05) : 185 - 187
[8] Selective and efficient oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals with n-butyltriphenylphosphonium peroxodisulfate (BunPPh3)2S2O8
Mohammadpoor-Baltork, I
Hajipour, AR
Aghajari, M
SYNTHETIC COMMUNICATIONS, 2002, 32 (09) : 1311 - 1317
[9] An easy and fast method for oxidative deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers, and ethylene acetals with KMnO4 supported on alumina under solvent-free conditions
Hajipour, AR
Mallakpour, SE
Baltork, IM
Backnezhad, H
SYNTHETIC COMMUNICATIONS, 2002, 32 (05) : 771 - 779
[10] Dinitrogen tetraoxide complexes of iron(III) and copper(II) nitrates as versatile reagents for organic syntheses. Efficient oxidative deprotection of silyl or tetrahydropyranyl ethers, acetals, and thioacetals
Firouzabadi, H
Iranpoor, N
Zolfigol, MA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (09) : 2169 - 2173

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