Efficient acetalisation of aldehydes catalyzed by titanium tetrachloride in a basic medium

被引：78

作者：

Clerici, A ^{[1
]}

Pastori, N ^{[1
]}

Porta, O ^{[1
]}

机构：

[1] Dipartiment Chim Politecnico, I-20131 Milan, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 51期

关键词：

D O I：

10.1016/S0040-4020(98)00982-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acetalisation of aliphatic and aromatic aldehydes is achieved in a basic medium by using catalytic amount of Ti(IV) chloride in MeOH in the presence of NH3 or Et3N. The present protocol shows many advantages over the well known base or acid catalysis: in fact, in contrast to base-promoted acetalisation, aldehydes with electron-rich carbonyl groups react easily enolizable aldehydes do not undergo aldol condensation and, in contrast to acid-catalysis, migration of the double bond does not occur in the preparation of alpha,beta-unsaturated acetals. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：15679 / 15690

页数：12

相关论文

共 52 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].

ALEXAKIS, A ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511

[2] CONVERSION OF ACETALS AND KETALS TO CARBONYL-COMPOUNDS PROMOTED BY TITANIUM TETRACHLORIDE [J].

BALME, G ;

GORE, J .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19) :3336-3338

[3] ACETAL FORMATION FOR KETONES AND AROMATIC ALDEHYDES WITH METHANOL [J].

BELL, JM ;

KUBLER, DG ;

SARTWELL, P ;

ZEPP, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4284-&

[4] STEREOMUTATION OF METHOXYCARBENIUM IONS .2. EXPERIMENTAL-EVIDENCE FOR AN INVERSION PROCESS [J].

BLACKBURN, C ;

CHILDS, RF ;

CREMER, D ;

GAUSS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2442-2448

[5] 1ST MEASUREMENTS OF ABSOLUTE RATE CONSTANTS FOR OXACARBENE INTERMEDIATES PRODUCED IN THE PHOTOCHEMISTRY OF BENZOCYCLOBUTENEDIONE [J].

BOATE, DR ;

JOHNSTON, LJ ;

KWONG, PC ;

LEERUFF, E ;

SCAIANO, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :8858-8863

[6]

BOX V, 1980, HETEROCYCLES, V14, P1713

[7] PREPARATION AND DISPROPORTIONATIVE-HYDROLYSIS OF CYCLOPROPANONE THIOACETALS - NEW METHOD OF HOMOLOGATION [J].

BRAUN, M ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (02) :669-691

[8] PHOTO-ISOMERIZATION AND THERMAL-ISOMERIZATION OF SOME 1-METHOXYALLYL CATIONS [J].

CHILDS, RF ;

HAGAR, ME .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (17) :1788-1794

[9]

COREY EJ, 1976, TETRAHEDRON LETT, P809

[10] OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].

COREY, EJ ;

ERICKSON, BW .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&

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