Salt effect on the endo/exo ratio of the reaction of cyclopentadiene with methyl methacrylate

被引:7
作者
Deshpande, SS
Phalgune, UD
Kumar, A [1 ]
机构
[1] Natl Chem Lab, Div Phys Chem, Pune 411008, Maharashtra, India
[2] Natl Chem Lab, OCS Div, Pune 411008, Maharashtra, India
关键词
salting-out; Diels-Alder reaction; salt solution;
D O I
10.1016/S0040-4020(02)01055-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The salt effect on the stereoselectivity of the reaction of cyclopentadiene with methyl methacrylate has been investigated. CaCl2, Na2SO4, KCl and LiCl enhance the endolexo ratios, while guanidinium chloride (GnCl) and LiClO4 decrease them. The results are supported by independent calculations of salting-out and in coefficients. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:8759 / 8762
页数:4
相关论文
共 46 条
[1]   CORRELATION OF SOLVENT EFFECTS ON STEREOSELECTIVITIES OF DIELS-ALDER REACTIONS BY MEANS OF LINEAR FREE ENERGY RELATIONSHIPS - A NEW EMPIRICAL MEASURE OF SOLVENT POLARITY [J].
BERSON, JA ;
MUELLER, WA ;
HAMLET, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (02) :297-&
[2]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[3]   SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS [J].
BRESLOW, R ;
MAITRA, U ;
RIDEOUT, D .
TETRAHEDRON LETTERS, 1983, 24 (18) :1901-1904
[4]   CHAOTROPIC SALT EFFECTS IN A HYDROPHOBICALLY ACCELERATED DIELS-ALDER REACTION [J].
BRESLOW, R ;
RIZZO, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4340-4341
[5]   QUANTITATIVE ANTIHYDROPHOBIC EFFECTS AS PROBES FOR TRANSITION-STATE STRUCTURES .1. BENZOIN CONDENSATION AND DISPLACEMENT-REACTIONS [J].
BRESLOW, R ;
CONNERS, RV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6601-6602
[6]   ELECTRONIC ABSORPTION SPECTRA OF CARBOXYLATE DERIVATIVES .3. EFFECTS OF SOLVENT AND STRUCTURE ON ABSORPTION SPECTRA OF ALPHA,BETA-UNSATURATED ESTERS [J].
CLOSSON, WD ;
BRADY, SF ;
ORENSKI, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4026-&
[7]  
Debye V.P., 1925, PHYS Z, V26, P22
[8]   Activation and reaction volumes in solution. 3 [J].
Drljaca, A ;
Hubbard, CD ;
van Eldik, R ;
Asano, T ;
Basilevsky, MV ;
le Noble, WJ .
CHEMICAL REVIEWS, 1998, 98 (06) :2167-2289
[9]   EFFECT OF MICRO-EMULSIONS ON THE DIELS-ALDER REACTION - ENDO EXO RATIOS IN THE REACTION OF CYCLOPENTADIENE AND METHYL-METHACRYLATE [J].
GONZALEZ, A ;
HOLT, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3186-3188
[10]  
Grieco P. A., 1991, ALDRICHIM ACTA, V24, P59