INDUCTIVE EFFECTS IN NEIGHBORING-GROUP PARTICIPATION - DESTABILIZATION OF CARBOCATIONS BY CC DOUBLE-BONDS IN SOLVOLYSES OF 2,2,5,5-TETRAMETHYLCYCLOPENT-3-EN-1-YL TOSYLATES

被引:14
作者
BENTLEY, TW
IRRGANG, B
MAYR, H
SCHLEYER, PV
机构
[1] MED UNIV LUBECK,INST CHEM,D-2400 LUBECK,FED REP GER
[2] UNIV ERLANGEN NURNBERG,INST ORGAN CHEM,D-8520 ERLANGEN,FED REP GER
关键词
D O I
10.1021/jo00250a015
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:3492 / 3498
页数:7
相关论文
共 73 条
[1]   PHOTOCHEMICAL DECARBONYLATION OF 2,2,4,4-TETRAMETHYL-6-OXABICYCLO[3.1.0]HEXAN-3-ONE - AN ENTRY INTO THE DIRADICAL MANIFOLD OF THE NOVEL 3-OXA-DI-PI-METHANE REARRANGEMENT [J].
ADAM, W ;
BERKESSEL, A ;
KRIMM, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4556-4561
[2]   CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134
[3]   INTRAMOLECULAR OLEFINIC ALDEHYDE PRINS REACTIONS FOR THE CONSTRUCTION OF 5-MEMBERED RINGS [J].
ANDERSEN, NH ;
HADLEY, SW ;
KELLY, JD ;
BACON, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :4144-4151
[4]  
ANDO T, 1979, TETRAHEDRON LETT, P121
[5]   NEIGHBORING GROUP PARTICIPATION IN SOLVOLYSIS .7. TRIFLUOROACETOSIS OF OMEGA-PHENYLALKYL 6-METHYL-2-NAPHTHALENESULFONATES [J].
ANDO, T ;
YAMAWAKI, J ;
SAITO, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (01) :219-224
[6]   SYNTHESIS OF 1,1,2,2,3,3-HEXAMETHYL-4,5-BIS(METHYLENE)CYCLOPENTANE [J].
BARAN, J ;
KLEIN, H ;
SCHADE, C ;
WILL, E ;
KOSCHINSKY, R ;
BAUML, E ;
MAYR, H .
TETRAHEDRON, 1988, 44 (08) :2181-2184
[7]   MECHANISTIC APPLICATIONS OF HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY - RATE-PRODUCT CORRELATIONS FOR COMPETING SOLVOLYSIS AND AMINOLYSIS OF BENZOYL CHLORIDE [J].
BENTLEY, TW ;
FREEMAN, AE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06) :1115-1119
[8]   EVIDENCE AGAINST APPRECIABLE HIDDEN RETURN IN SOLVOLYSES OF SIMPLE SECONDARY SUBSTRATES [J].
BENTLEY, TW ;
LIGGERO, SH ;
IMHOFF, MA ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (06) :1970-1973
[9]   ACCURATE KINETIC-STUDIES BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
BENTLEY, TW ;
GREAM, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1776-1778
[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