INFLUENCE OF AN ALPHA-CYANO FUNCTION ON CHARGE DELOCALIZATION IN THE BENZYL CATION - RELATIONSHIP BETWEEN INDUCTIVE DESTABILIZATION AND CONJUGATIVE STABILIZATION BY THE CYANO GROUP

被引:54
作者
GASSMAN, PG
GUGGENHEIM, TL
机构
关键词
D O I
10.1021/jo00136a048
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:3023 / 3026
页数:4
相关论文
共 25 条
[1]   SOLVOLYTIC REACTIVITY OF 1-TRIFLUOROMETHYL-1-PHENYLETHYL TOSYLATE - FORMATION OF A HIGHLY DESTABILIZED CARBONIUM-ION [J].
ALLEN, AD ;
JANSEN, MP ;
KOSHY, KM ;
MANGRU, NN ;
TIDWELL, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) :207-211
[2]   DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].
BROWN, HC ;
OKAMOTO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987
[3]   GENERATION OF ALPHA-KETO CATIONS - QUANTITATIVE ASPECTS [J].
CREARY, X .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3938-3945
[4]   STABILIZATION OF ALPHA-KETO CATIONS BY CARBONYL CONJUGATION [J].
CREARY, X .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2463-2465
[5]   MESOMERIC STABILIZATION OF CARBONIUM-IONS BY ALPHA-CYANO GROUPS - A THEORETICAL EVALUATION OF INDUCTIVE VS RESONANCE EFFECTS OF THE CYANO MOIETY [J].
DIXON, DA ;
CHARLIER, PA ;
GASSMAN, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3957-3959
[7]   THE EFFECT OF THE ALPHA-CYANO MOIETY ON NEIGHBORING GROUP PARTICIPATION BY THE CYCLOPROPYL GROUP [J].
GASSMAN, PG ;
TALLEY, JJ .
TETRAHEDRON LETTERS, 1981, 22 (52) :5253-5256
[8]   SOLVOLYSIS OF ADAMANTANONE CYANOHYDRIN SULFONATES - AN EVALUATION OF H-ALPHA-CN VS H-BETA-CN RATE RATIOS [J].
GASSMAN, PG ;
SAITO, K ;
TALLEY, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) :7613-7615
[9]   ALPHA-CYANO GROUP AS A SUBSTITUENT IN SOLVOLYSIS REACTIONS - EVALUATION OF INDUCTIVE DESTABILIZATION VS MESOMERIC STABILIZATION OF CATIONS BY THE CYANO MOIETY [J].
GASSMAN, PG ;
TALLEY, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :1214-1216
[10]   EFFECT OF ALPHA-CYANO GROUPS ON NEIGHBORING GROUP PARTICIPATION IN CARBONIUM-ION REACTIONS [J].
GASSMAN, PG ;
TALLEY, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (12) :4138-4143