STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .29. SOLVOLYSIS OF TERTIARY ALLYLIC PARA-NITROBENZOATES - EFFECT OF ALLYLIC DOUBLE-BOND ON RATES OF SOLVOLYSIS OF REPRESENTATIVE TERTIARY PARA-NITROBENZOATES

被引:15
作者
BROWN, HC
RAO, CG
RAVINDRANATHAN, M
机构
关键词
D O I
10.1021/jo00420a009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:4939 / 4943
页数:5
相关论文
共 36 条
[1]   SN2-SN1 SPECTRUM .1. ROLE OF NUCLEOPHILIC SOLVENT ASSISTANCE AND NUCLEOPHILICALLY SOLVATED ION-PAIR INTERMEDIATES IN SOLVOLYSES OF PRIMARY AND SECONDARY ARENESULFONATES [J].
BENTLEY, TW ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7658-7666
[2]   THE EFFECT OF A CYCLOPROPYL GROUP ON A DISPLACEMENT REACTION AT AN ADJACENT SATURATED CARBON ATOM .1. THE ETHANOLYSIS OF CYCLOPROPYLMETHYL BENZENESULFONATE [J].
BERGSTROM, CG ;
SIEGEL, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (01) :145-151
[3]   THE ETHANOLYSIS OF ALLYL BENZENESULFONATE [J].
BERGSTROM, CG ;
SIEGEL, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (01) :254-256
[4]  
Brown, 1972, BORANES ORGANIC CHEM
[5]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .27. SOLVOLYSIS OF EXO-1,2-DIPHENYL-2-NORBORNYL AND ENDO-1,2-DIPHENYL-2-NORBORNYL AND ENDO-1,2-DIMETHYL-2-NORBORNYL PARA-NITROBENZOATES AND CHLORIDES - DEFINITIVE EVIDENCE FOR CLASSICAL NATURE OF 1,2-DISUBSTITUTED TERTIARY 2-NORBORNYL CATIONS AND IMPLICATIONS FOR STRUCTURE OF PARENT 2-NORBORNYL CATIONA [J].
BROWN, HC ;
RAVINDRANATHAN, M ;
RAO, CG ;
CHLOUPEK, FJ ;
REI, MH .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3667-3678
[6]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .22. EFFECT OF RING SIZE ON STABILIZATION OF DEVELOPING CARBOCATIONS AS REVEALED BY TOOL OF INCREASING ELECTRON DEMAND [J].
BROWN, HC ;
RAVINDRANATHAN, M ;
PETERS, EN ;
RAO, CG ;
RHO, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) :5373-5378
[7]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .26. CRITICAL STUDY OF EFFECT OF SOLVENT ON EXO-ENDO RATE RATIO IN SOLVOLYSIS OF 2-NORBORNYL DERIVATIVES - EVIDENCE THAT EXO-ENDO RATE RATIO IS NOT RESULT OF K-DELTA-K-S PROCESSES [J].
BROWN, HC ;
RAVINDRANATHAN, M ;
CHLOUPEK, FJ ;
ROTHBERG, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (10) :3143-3149
[8]   SOLVOLYSIS OF 3-ARYL-3-NORTRICYCLYL P-NITROBENZOATES - EVIDENCE FOR MAJOR INCREASES IN ELECTRON SUPPLY BY CYCLOPROPYL GROUP WITH INCREASING ELECTRON DEMAND AT CATIONIC CENTER [J].
BROWN, HC ;
PETERS, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (07) :1927-1929
[9]   CHEMICAL EFFECTS OF STERIC STRAINS .2. THE EFFECT OF STRUCTURE ON OLEFIN FORMATION IN THE HYDROLYSIS OF TERTIARY ALIPHATIC CHLORIDES [J].
BROWN, HC ;
FLETCHER, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (03) :1223-1226
[10]   I-STRAIN AS A FACTOR IN THE CHEMISTRY OF RING COMPOUNDS [J].
BROWN, HC ;
FLETCHER, RS ;
JOHANNESEN, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) :212-221