H-ALPHA-CN VERSUS H-BETA-CN RATE RATIOS IN THE SOLVOLYSIS OF SULFONATE ESTERS IN UNCONSTRAINED SYSTEMS - ADDITIONAL EVIDENCE FOR CONJUGATIVE STABILIZATION OF ATTACHED CARBOCATIONS BY THE CYANO MOIETY

被引：39

作者：

GASSMAN, PG

SAITO, K

机构：

来源：

TETRAHEDRON LETTERS | 1981年 / 22卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(01)90304-1

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：1311 / 1314

页数：4

相关论文

共 18 条

[1] GENERATION OF ALPHA-KETO CATIONS - QUANTITATIVE ASPECTS [J].

CREARY, X .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3938-3945

[2] 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

[3] SOLVOLYSIS OF 1-SUBSTITUTED-2-ADAMANTYL SULFONATES - BRIDGING OR NO BRIDGING [J].

FARCASIU, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (17) :5301-5305

[4] STERIC RELIEF CONTROL OF SOLVOLYSIS RATES OF 1-ALKYL-2-ADAMANTYL SUBSTRATES - EMPIRICAL FORCE-FIELD CALCULATIONS [J].

FARCASIU, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3878-3882

[5] 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

[6] 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

[7] INVOLVEMENT OF OXYGENATED FUNCTIONS IN ACETOLYSIS OF 7-OXYGENATED NORBORNYL TOSYLATES [J].

GASSMAN, PG ;

MACMILLA.JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) :5527-&

[8] SUBSTITUENT EFFECTS ON ACETOLYSIS OF EXO- AND ENDO-2-NORBORNYL TOSYLATES [J].

GASSMAN, PG ;

MARSHALL, JL ;

MACMILLA.JG ;

HORNBACK, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (15) :4282-+

[9] ACETOLYSIS OF EPIMERIC 3,3-DIMETHYL-7-TOSYLOXYBICYCLO-[2.2.1]HEPTAN-2-ONES . INTERACTION BETWEEN INCIPIENT CARBONIUM IONS AND NEIGHBORING NONENOLIZABLE KETONES [J].

GASSMAN, PG ;

HORNBACK, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) :5817-&

[10] SYNTHESIS AND ACETOLYSIS OF EPIMERIC 7-TOSYLOXYNORBORNAN-2-ONES [J].

GASSMAN, PG ;

MARSHALL, JL ;

HORNBACK, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) :5811-&