A CHEMICAL, SPECTROSCOPIC, AND THEORETICAL ASSESSMENT OF THE LEWIS ACIDITY OF LICLO4 IN DIETHYL-ETHER

被引：51

作者：

PAGNI, RM

KABALKA, GW

BAINS, S

PLESCO, M

WILSON, J

BARTMESS, J

机构：

[1] Department of Chemistry, University of Tennessee, Knoxville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 11期

关键词：

D O I：

10.1021/jo00063a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Moderate diastereoselectivity is observed in the reaction of cyclopentadiene with dimethyl maleate and optically active dimenthyl fumarate in LiClO4/diethyl ether. Moderate regioselectivity is also seen in the reaction of isoprene and methyl acrylate in the same medium. NMR experiments and MNDO calculations, in conjunction with published work on Li+ in the gas phase, demonstrate that the strong, intrinsic Lewis acidity of Li+ is moderated in ether by complexation to the solvent and the counterion.

引用

页码：3130 / 3133

页数：4

共 59 条

[1]

ALDER K, 1955, LIEBIGS ANN CHEM, V593, P1

[2]

[Anonymous], 1985, SUPERACIDS

[3]

BAINS S, 1991, TETRAHEDRON LETT, P5663

[4] TRANSITION STRUCTURES OF THE LEWIS ACID-CATALYZED DIELS-ALDER REACTION OF BUTADIENE WITH ACROLEIN - THE ORIGINS OF SELECTIVITY [J].