Tetrabutylammonium tribromide (TBATB)-promoted tetrahydropyranylation/depyranylation of alcohols

被引：106
作者：
Naik, S [1 ]
Gopinath, R [1 ]
Patel, BK [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, India
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 43期
关键词：
D O I：
10.1016/S0040-4039(01)01599-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Alcohols are tetrahydropyranylated rapidly in high yields in the presence of a catalytic amount of TBATB in dichloromethane at room temperature. Depyranylation to their parent alcohol is achieved in quantitative yields by merely changing the solvent to methanol. (C) 2001 Elsevier Science Ltd. All rights reserved.
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页码：7679 / 7681
页数：3
相关论文
共 29 条
[1]  
Babu BS, 1999, SYNLETT, P1261
[2]   Mild and efficient tetrahydropyranylation of alcohols-catalysis by lithium percholorate in diethyl ether. [J].
Babu, BS ;
Balasubramanian, KK .
TETRAHEDRON LETTERS, 1998, 39 (50) :9287-9288
[3]   Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2:: An environmentally favorable synthetic protocol [J].
Bora, U ;
Bose, G ;
Chaudhuri, MK ;
Dhar, SS ;
Gopinath, R ;
Khan, AT ;
Patel, BK .
ORGANIC LETTERS, 2000, 2 (03) :247-249
[4]   A convenient and useful method of preparation of α-bromo enones from the corresponding enones using organic ammonium tribromide (OATB) [J].
Bose, G ;
Barua, PMB ;
Chaudhuri, MK ;
Kalita, D ;
Khan, AT .
CHEMISTRY LETTERS, 2001, (04) :290-291
[5]   Ionic liquids as recyclable reaction media for the tetrahydropyranylation of alcohols [J].
Branco, LC ;
Afonso, CAM .
TETRAHEDRON, 2001, 57 (20) :4405-4410
[6]   An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB) [J].
Chaudhuri, MK ;
Khan, AT ;
Patel, BK ;
Dey, D ;
Kharmawophlang, W ;
Lakshmiprabha, TR ;
Mandal, GC .
TETRAHEDRON LETTERS, 1998, 39 (44) :8163-8166
[7]   Zirconium sulfophenyl phosphonate as a heterogenous catalyst in tetrahydropyranylation of alcohols and phenols. [J].
Curini, M ;
Epifano, F ;
Marcotullio, MC ;
Rosati, O ;
Costantino, U .
TETRAHEDRON LETTERS, 1998, 39 (44) :8159-8162
[8]   CuCl2.H2O-MeOH.: A new reagent system for the deprotection of tetrahydropyranyl ethers. [J].
Davis, KJ ;
Bhalerao, UT ;
Rao, BV .
SYNTHETIC COMMUNICATIONS, 2000, 30 (13) :2301-2308
[9]   Microwave-mediated selective monotetrahydropyranylation of symmetrical diols catalyzed by iodine [J].
Deka, N ;
Sarma, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06) :1947-1948
[10]   Microwave assisted catalytic protection and deprotection of alcohols with 3,4-dihydro-2H-pyran [J].
Deka, N ;
Sarma, JC .
SYNTHETIC COMMUNICATIONS, 2000, 30 (24) :4435-4441
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