Selectivities of Diels-Alder reactions catalyzed by highly acidic boronated aluminas

被引：15

作者：

McGinnis, MB ^{[1
]}

Vagle, K ^{[1
]}

Green, JF ^{[1
]}

Tan, LC ^{[1
]}

Palmer, R ^{[1
]}

Siler, J ^{[1
]}

Pagni, RM ^{[1
]}

Kabalka, GW ^{[1
]}

机构：

[1] UNIV TENNESSEE,DEPT CHEM,KNOXVILLE,TN 37996

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 10期

关键词：

D O I：

10.1021/jo951077m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of boronated aluminas was prepared by the reaction of BX(3) (X = F, Cl, Br) with alumina or by a two-step synthesis involving the reaction of BH3 . Me(2)S with alumina and then with I-2. The modified aluminas, BX(n)/Al2O3, were found to have n = 3 (F), n = 1.5 (Cl), n = 1 (Br), and n = = 1 (Ii. The acidity of the solids (indicator dyes) was large and decreased in the order I similar to Br > Cl > F. The solids catalyzed the Diels-Alder reactions of methyl acrylate with cyclopentadiene and isoprene with methyl acrylate, both of which occurred in high yield and with high selectivity. The regioselectivity of the isoprene/methyl acrylate reaction in fact is higher than seen previously. The results of the heterogeneous reactions were compared to those catayzed by B-bromo- and B-chlorocatecholborane, which serve as models for the boronated aluminas.

引用

页码：3496 / 3500

页数：5

共 29 条

[1] DIASTEREOSELECTIVITIES IN THE DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH OPTICALLY-ACTIVE DIMENTHYL FUMARATE AND MENTHYL METHYL FUMARATE IN LICLO4/ETHER AND ON AL2O3 [J].