ADDITIONS TO BICYCLIC OLEFINS .9. ELECTROPHILIC ADDITION OF ACETIC-ACID AND PERDEUTERIOACETIC ACID TO NORBORNENE AND 7,7-DIMETHYLNORBORNENE - REMARKABLE STEREOSELECTIVITY FOR ADDITION PROCESS WITH EVIDENCE FOR CAPTURE OF 2-NORBORNYL CATION IN AN UNSYMMETRICAL (CLASSICAL) STATE

被引：26

作者：

BROWN, HC ^{[1
]}

KAWAKAMI, JH ^{[1
]}

机构：

[1] PURDUE UNIV,RICHARD B WETHERILL LAB,W LAFAYETTE,IN 47907

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1975年 / 97卷 / 19期

关键词：

D O I：

10.1021/ja00852a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

引用

页码：5521 / 5526

页数：6

共 38 条

[1] A REMARKABLY HIGH STEREOSELECTIVITY IN ADDITION OF ACETIC ACID AND TRIFLUOROACETIC ACID TO NORBORNENE - EVIDENCE OF CAPTURE OF NORBORNYL CATION IN AN UNSYMMETRICAL STATE [J].

BROWN, HC ;

KAWAKAMI, JH ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5536-&

[2] EXO-CIS ADDITION OF TRIFLUOROACETIC ACID AND ACETIC ACID TO 7,7-DIMETHYLNORBORNENE - EVIDENCE FOR ESSENTIAL ABSENCE OF MOLECULAR CYCLIC ADDITION PROCESSES [J].

BROWN, HC ;

KAWAKAMI, JH ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (12) :3816-&

[3] ADDITIONS TO BICYCLIC OLEFINS .7. ELECTROPHILIC ADDITION OF HYDROGEN-CHLORIDE AND DEUTERIUM CHLORIDE TO NORBORNENE, 2-METHYLENENORBORNANE, AND RELATED BICYCLIC OLEFINS - EVIDENCE FOR A CARBONIUM-ION PROCESS AND CAPTURE OF UNSYMMETRICAL (CLASSICAL) 2-NORBORNYL CATIONS [J].

BROWN, HC ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :600-610

[4] STEREOCHEMISTRY OF ADDITIONS TO NORBORNENE AND 7,7-DIMETHYLNORBORNENE . A NEW INTERPRETATION OF STERIC INFLUENCE OF 7,7-DIMETHYL SUBSTITUENTS ON REACTIONS OF NORBORNYL SYSTEM [J].

BROWN, HC ;

KAWAKAMI, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (01) :201-&

[5] ADDITIONS TO BICYCLIC OLEFINS .8. ELECTROPHILIC ADDITION OF TRIFLUOROACETIC-ACID AND DEUTERIOTRIFLUORACETIC ACID TO NORBORNENE AND RELATED BICYCLIC OLEFINS - EVIDENCE FOR CAPTURE OF UNSYMMETRICAL (CLASSICAL) 2-NORBORNYL CATION [J].

BROWN, HC ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (09) :2469-2476

[6] QUESTION OF SIGMA-BRIDGING IN SOLVOLYSIS OF 2-NORBORNYL DERIVATIVES [J].

BROWN, HC .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (11) :377-386

[7] ADDITIONS TO BICYCLIC OLEFINS .6. STEREOCHEMISTRY OF OXYMERCURATION-DEMERCURATION OF NORBORNENE, 7,7-DIMETHYLNORBORNENE, AND RELATED OLEFINS [J].

BROWN, HC ;

KAWAKAMI, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (26) :8665-8669

[8] FORMATION OF ENDO-2-PHENYLTHIO-EXO-3-CHLORO-7,7-DIMETHYLNORBORNANE FROM ADDITION OF BENZENESULFENYL CHLORIDE TO 7,7-DIMETHYLNORBORNEN - FURTHER EVIDENCE FOR DOMINANT STERIC CONTROL BY 7,7-DIMETHYL SUBSTITUENTS ON DIRECTION ADDITIONS TO NORBORNENE MOIETY [J].

BROWN, HC ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (11) :3502-&

[9] ADDITIONS TO BICYCLIC OLEFINS .1. STEREOCHEMISTRY OF HYDROBORATION OF NORBORNENE, 7,7-DIMETHYLNORBORNENE, AND RELATED BICYCLIC OLEFINS - STERIC EFFECTS IN 7,7-DIMETHYLNORBORNYL SYSTEM [J].

BROWN, HC ;

KAWAKAMI, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (07) :1990-+

[10] 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

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