The Claisen rearrangement. Response to solvents and substituents: The case for both hydrophobic and hydrogen bond acceleration in water and for a variable transition state

被引:166
作者
Gajewski, JJ
机构
[1] Department of Chemistry, Indiana University, Bloomington
关键词
D O I
10.1021/ar9600493
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[No abstract available]
引用
收藏
页码:219 / 225
页数:7
相关论文
共 78 条
[1]   SUBSTITUTION AT SATURATED CARBON .26. A COMPLETE ANALYSIS OF SOLVENT EFFECTS ON INITIAL STATES AND TRANSITION-STATES FOR THE SOLVOLYSIS OF THE TERT-BUTYL HALIDES IN TERMS OF G, H, AND S USING THE UNIFIED METHOD [J].
ABRAHAM, MH ;
GRELLIER, PL ;
NASEHZADEH, A ;
WALKER, RAC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (09) :1717-1724
[2]   SOLVENT EFFECTS IN ORGANIC-CHEMISTRY - RECENT DEVELOPMENTS [J].
ABRAHAM, MH ;
GRELLIER, PL ;
ABBOUD, JLM ;
DOHERTY, RM ;
TAFT, RW .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (11) :2673-2686
[3]   SECONDARY TRITIUM ISOTOPE EFFECTS AS PROBES OF THE ENZYMIC AND NON-ENZYMIC CONVERSION OF CHORISMATE TO PREPHENATE [J].
ADDADI, L ;
JAFFE, EK ;
KNOWLES, JR .
BIOCHEMISTRY, 1983, 22 (19) :4494-4501
[4]  
ALBERY WJ, 1967, PROGR REACTION KINET, V4, P353
[5]   INITIAL-STATE AND TRANSITION-STATE EFFECTS ON DIELS-ALDER REACTIONS IN WATER AND MIXED AQUEOUS SOLVENTS [J].
BLOKZIJL, W ;
ENGBERTS, JBFN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5440-5442
[6]   EFFECT OF POLAR-SOLVENTS ON THE RATES OF CLAISEN REARRANGEMENTS - ASSESSMENT OF IONIC CHARACTER [J].
BRANDES, E ;
GRIECO, PA ;
GAJEWSKI, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :515-516
[7]   QUANTITATIVE ANTIHYDROPHOBIC EFFECTS AS PROBES FOR TRANSITION-STATE STRUCTURES .2. DIELS-ALDER REACTIONS [J].
BRESLOW, R ;
ZHU, ZN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (39) :9923-9924
[8]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[10]   SUBSTITUENT EFFECTS ON THE ALIPHATIC CLAISEN REARRANGEMENT .1. SYNTHESIS AND REARRANGEMENT OF CYANO-SUBSTITUTED ALLYL VINYL ETHERS [J].
BURROWS, CJ ;
CARPENTER, BK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) :6983-6984