THE PRESSURE EFFECT IN PERICYCLIC REARRANGEMENTS - THE COPE REARRANGEMENT, ELECTROCYCLIZATION, AND THE INTRAMOLECULAR DIELS-ALDER REACTION

被引：24

作者：

DIEDRICH, MK ^{[1
]}

HOCHSTRATE, D ^{[1
]}

KLARNER, FG ^{[1
]}

ZIMNY, B ^{[1
]}

机构：

[1] UNIV ESSEN GESAMTHSCH,INST ORGAN CHEM,D-45117 ESSEN,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 10期

关键词：

D O I：

10.1002/anie.199410791

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Important information about the geometry of the transition state is contained in the activation volume ΔV≠ obtained from the pressure dependence of the reaction rate, which in the title reactions allows a correlation to be drawn between the size of the activation volume and the number of new interactions in the cyclic transition states. Every additional five‐ or six‐membered ring formed in the transition state contributes about −10 to −12cm3mol−1 to ΔV≠. Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1079 / 1081

页数：3

共 36 条

[1]

ARTSCHWAGERPERL U, 1989, THESIS RUHR U

[2]

ASANO T, 1973, REV PHYS CHEM JPN, V43, P82

[3] ACTIVATION AND REACTION VOLUMES IN SOLUTION [J].

ASANO, T ;

LENOBLE, J .

CHEMICAL REVIEWS, 1978, 78 (04) :407-489

[4] THE INFLUENCE OF SUBSTITUENT INDUCED ASYNCHRONICITY ON THE STEREOCHEMISTRIES OF INTRAMOLECULAR DIELS-ALDER REACTIONS [J].

BROWN, FK ;

HOUK, KN .

TETRAHEDRON LETTERS, 1985, 26 (19) :2297-2300

[5] FORBIDDEN REACTIONS - [2 + 2] CYCLOREVERSION OF RIGID CYCLOBUTANES [J].

DOERING, WV ;

ROTH, WR ;

BREUCKMANN, R ;

FIGGE, L ;

LENNARTZ, HW ;

FESSNER, WD ;

PRINZBACH, H .

CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01) :1-9

[6]

HOCHSTRATE D, 1992, THESIS RUHR U BOCHUM

[7] TRANSITION STRUCTURES OF HYDROCARBON PERICYCLIC-REACTIONS [J].

HOUK, KN ;

LI, Y ;

EVANSECK, JD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (06) :682-708

[8]

HOUK KN, 1985, TETRAHEDRON LETT, V26, P2269

[9]

HOUK KN, 1992, ANGEW CHEM, V104, P711

[10] REACTIONS AT HIGH-PRESSURE .10. THE VOLUME PROFILE OF AN INTRAMOLECULAR DIELS-ALDER REACTION [J].

ISAACS, NS ;

VANDERBEEKE, P .

TETRAHEDRON LETTERS, 1982, 23 (20) :2147-2148

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