ORIGIN OF HUISGEN FACTOR-X - STAGGERING OF ALLYLIC BONDS PROMOTES ANOMALOUSLY RAPID EXO ATTACK ON NORBORNENES

被引:110
作者
RONDAN, NG [1 ]
PADDONROW, MN [1 ]
CARAMELLA, P [1 ]
MAREDA, J [1 ]
MUELLER, PH [1 ]
HOUK, KN [1 ]
机构
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
关键词
D O I
10.1021/ja00382a052
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:4974 / 4976
页数:3
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共 30 条
[1]   ALKENE REACTIVITIES IN TRIFLUOROACETIC-ACID - A COMPARISON OF NORBORNENE AND PROTOADAMANTENE IN TRIFLUOROACETIC-ACID AND AQUEOUS ACID [J].
ALLEN, AD ;
TIDWELL, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) :3145-3149
[2]   CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134
[3]  
ANH NT, 1977, NOUV J CHIM, V1, P161
[4]   SOLVOLYTIC BEHAVIOUR OF EXO- AND ENDO-BICYCLO[3,2,1]OCTANE-6-TOLUENE-P-SULPHONATES [J].
APPLETON, RA ;
FAIRLIE, JC ;
MCCRINDLE, R ;
PARKER, W .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (14) :1716-+
[5]   STEREOSELECTIVE SYNTHESIS OF 3-EXO-SUBSTITUTED 2-ENDO-ACYL-5-NORBORNENE DERIVATIVES [J].
BALDWIN, SW ;
TOMESCH, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (16) :2382-2385
[6]   1,3-DIPOLAR CYCLOADDITIONS .73. RELATIVE DIPOLAROPHILE ACTIVITIES IN CYCLOADDITIONS OF BENZONITRILE OXIDE [J].
BAST, K ;
CHRISTL, M ;
HUISGEN, R ;
MACK, W .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (10) :3312-3344
[7]   EXO-ENDO RELATIVE REACTIVITIES IN 3 REPRESENTATIVE U-SHAPED SYSTEMS . EXO-ENDO RATE RATIO IN SOLVOLYSIS AS A STERIC PHENOMENON [J].
BROWN, HC ;
HAMMAR, WJ ;
KAWAKAMI, JH ;
ROTHBERG, I ;
VANDERJA.DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (24) :6381-&
[8]   QUESTION OF SIGMA-BRIDGING IN SOLVOLYSIS OF 2-NORBORNYL DERIVATIVES [J].
BROWN, HC .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (11) :377-386
[9]   ADDITIONS TO BICYCLIC OLEFINS .5. EFFECT OF 7,7-DIMETHYL SUBSTITUENTS ON STEREOCHEMISTRY AND RATES OF CYCLIC ADDITIONS TO NORBORNENES [J].
BROWN, HC ;
KAWAKAMI, JH ;
LIU, KT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2209-2216
[10]   CONCEPTUAL-MODEL OF THROUGH-BONDS INTERACTIONS [J].
BRUNCK, TK ;
WEINHOLD, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (15) :4392-4393