An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdophosphoric acid

被引：93

作者：

Heravi, Majid M. ^{[1
]}

Bakhtiari, Khadijeh

Bamoharram, Fatemeh F.

机构：

[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran 1234, Iran

[2] Azad Univ Mashad, Dept Chem, Mashhad, Iran

来源：

CATALYSIS COMMUNICATIONS | 2006年 / 7卷 / 07期

关键词：

acylals; protection; 1,1-diacetates; heteropoly acid; 12-molybdophosphoric acid; deprotection;

D O I：

10.1016/j.catcom.2006.01.003

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A variety of aromatic aldehydes react with acetic anhydride in the presence of catalytic amount of 12-molybdophosphoric acid, H3PMo12O40, to afford the corresponding 1,1-diacetates (acylals), in excellent yields. Ketones are not affected under the reaction conditions. The catalyst in dry acetone has also been successfully applied for deprotection of the resulting acylals. (c) 2006 Published by Elsevier B.V.

引用

页码：499 / 501

页数：3

共 37 条

[1] Bismuth compounds in organic synthesis. Bismuth nitrate catalyzed chemoselective synthesis of acylals from aromatic aldehydes [J].

Aggen, DH ;

Arnold, JN ;

Hayes, PD ;

Smoter, NJ ;

Mohan, RS .

TETRAHEDRON, 2004, 60 (16) :3675-3679

[2] COBALT(II)-CATALYZED REACTION OF ALDEHYDES WITH ACETIC-ANHYDRIDE UNDER AN OXYGEN ATMOSPHERE - SCOPE AND MECHANISM [J].

BHATIA, B ;

PUNNIYAMURTHY, T ;

IQBAL, J .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5518-5523

[3] Aluminum dodecatungstophosphate (AlPW12O40) as an efficient heterogeneous inorganic catalyst for the chemoselective synthesis of geminal diacetates (acylals) under solvent-free conditions [J].

Firouzabadi, H ;

Iranpoor, N ;

Nowrouzi, F ;

Amani, K .

TETRAHEDRON LETTERS, 2003, 44 (20) :3951-3954

[4] Tungstophosphoric acid (H3PW12O40) as a heterogeneous inorganic catalyst.: Activation of hexamethyldisilazane (HMDS) by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions [J].

Firouzabadi, H ;

Iranpoor, N ;

Amani, K ;

Nowrouzi, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2601-2604

[5] PREPARATION AND SPECTRAL PROPERTIES OF BENZYLIDENE DIACETATES [J].

FREEMAN, F ;

KARCHEFSKI, EM .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1977, 22 (03) :355-357

[6] EVIDENCE FOR A CYCLIC AA11 MECHANISM IN HYDROLYSIS OF BENZYLIDENE DIACETATES [J].

GREGORY, MJ .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (06) :1201-&

[7] A convenient oxidative deprotection of tetrahydropyranyl ethers with iron(III) nitrate and clay under microwave irradiation in solvent free conditions [J].

Heravi, MM ;

Ajami, D ;

Mojtahedi, MM ;

Ghassemzadeh, M .

TETRAHEDRON LETTERS, 1999, 40 (03) :561-562

[8]

Heravi MM, 2005, J CHEM RES, P105

[9] Zeofen, an eco-friendly catalyst for deoximation under microwave irradiation in solventless system [J].

Heravi, MM ;

Ajami, D ;

Mohajerani, B ;

Tabar-Hydar, K ;

Ghassemzadeh, M .

SYNTHETIC COMMUNICATIONS, 2002, 32 (21) :3325-3330

[10] 'Zeofen', a user-friendly oxidizing reagent [J].

Heravi, MM ;

Ajami, D ;

Aghapoor, K ;

Ghassemzadeh, M .

CHEMICAL COMMUNICATIONS, 1999, (09) :833-834

← 1 2 3 4 →