REMOTE INDUCTIVE EFFECTS IN THE SOLVOLYSIS OF SECONDARY AND TERTIARY 2-NORBORNYL DERIVATIVES - EVIDENCE FOR NONCLASSICAL STABILIZATION OF THE 2-NORBORNYL CATION

被引:67
作者
LENOIR, D
APELOIG, Y
ARAD, D
SCHLEYER, PV
机构
[1] TECHNION ISRAEL INST TECHNOL, DEPT CHEM, IL-32000 HAIFA, ISRAEL
[2] UNIV ERLANGEN NURNBERG, INST ORGAN CHEM, D-8520 ERLANGEN, FED REP GER
关键词
D O I
10.1021/jo00238a033
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:661 / 675
页数:15
相关论文
共 148 条
[1]   DARSTELLUNG UND VERHALTEN VON BICYCLO-[1.2.3]-NONEN BERITRAGE ZUR KENNTNIS DER WAGNERSCHEN UMLAGERUNG UND DER PHENYLAZID-REAKTION [J].
ALDER, K ;
KRIEGER, H ;
WEISS, H .
CHEMISCHE BERICHTE-RECUEIL, 1955, 88 (01) :144-155
[2]   NORBORNANES .19. THE INDUCTIVE MODEL FOR NORBORNYL CATION FORMATION [J].
ALTMANNSCHAFFNER, E ;
GROB, CA .
HELVETICA CHIMICA ACTA, 1987, 70 (01) :43-48
[3]  
[Anonymous], ANGEW CHEM
[4]   MOLECULAR-ORBITAL THEORY OF ELECTRONIC-STRUCTURE OF MOLECULES .35. BETA-SUBSTITUENT EFFECTS ON STABILITIES OF ETHYL AND VINYL CATIONS - COMPARISON WITH ISOELECTRONIC METHYL BORANES - RELATIVE IMPORTANCE OF HYPERCONJUGATIVE AND INDUCTIVE EFFECT [J].
APELOIG, Y ;
SCHLEYER, PV ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (18) :5901-5909
[5]  
APELOIG Y, 1981, TETRAHEDRON LETT, P879
[6]  
ARAD D, UNPUB
[7]   SN2 DISPLACEMENTS AT 2-NORBORNYL BROSYLATES [J].
BANERT, K ;
KIRMSE, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) :3766-3767
[8]  
BARKHASH VA, 1984, TOP CURR CHEM, V116, P1
[9]  
BEAUCHAMP JL, UNPUB
[10]   THE SN2-SN1 SPECTRUM .3. SOLVOLYSES OF SECONDARY AND TERTIARY ALKYL SULFONATES IN FLUORINATED ALCOHOLS - FURTHER EVIDENCE FOR THE SN2 (INTERMEDIATE) MECHANISM [J].
BENTLEY, TW ;
BOWEN, CT ;
MORTEN, DH ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5466-5475