SOLVENT EFFECTS ON ENDO/EXO SELECTIVITIES IN (4 + 2) CYCLOADDITIONS OF CYANOETHYLENES

被引：32

作者：

KARCHER, T

SICKING, W

SAUER, J

SUSTMANN, R

机构：

[1] UNIV ESSEN GESAMTHSCH,INST ORGAN CHEM,POSTFACH 103,W-4300 ESSEN 1,GERMANY

[2] UNIV REGENSBURG,INST ORGAN CHEM,W-8400 REGENSBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)74708-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SCRF calculations on transition structures of cycloadditions of acrylonitrile and maleonitrile to cyclopentadiene and 1,3-butadiene show that the experimentally observed endo preference for the cycloaddition of acrylonitrile to cyclopentadiene is the consequence of solvent influence and not the result of secondary orbital interactions.

引用

页码：8027 / 8030

页数：4

共 15 条

[1] [Anonymous], 1969, ANGEW CHEM
[2] [Anonymous], 1980, ANGEW CHEM, DOI 10.1002/ange.19800921004
[3] MECHANISM OF THE DIELS-ALDER REACTION - REACTIONS OF BUTADIENE WITH ETHYLENE AND CYANOETHYLENES
DEWAR, MJS
OLIVELLA, S
STEWART, JJP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 5771 - 5779
[4] SUBSTITUENT EFFECTS AND TRANSITION STRUCTURES FOR DIELS-ALDER REACTIONS OF BUTADIENE AND CYCLOPENTADIENE WITH CYANOALKENES
HOUK, KN
LONCHARICH, RJ
BLAKE, JF
JORGENSEN, WL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9172 - 9176
[5] HOUK KN, 1992, ANGEW CHEM, V104, P711
[6] ELECTROSTATIC INTERACTION OF A SOLUTE WITH A CONTINUUM - IMPROVED DESCRIPTION OF THE CAVITY AND OF THE SURFACE CAVITY BOUND CHARGE-DISTRIBUTION
PASCUALAHUIR, JL
SILLA, E
TOMASI, J
BONACCORSI, R
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (06) : 778 - 787
[7] QUANTUM CHEMICAL APPROACH TO DIELECTRIC SOLVENT EFFECTS IN MOLECULAR LIQUIDS
RIVAIL, JL
RINALDI, D
[J]. CHEMICAL PHYSICS, 1976, 18 (1-2) : 233 - 242
[8] RIVAIL JL, GEOMOS QCPE584 PROGR
[9] EINE STUDIE DIELS-ALDER-REAKTION .I. REAKTIVITAT VON DIENOPHILEN GEGENUBER CYCLOPENTADIEN + 9.10-DIMETHYL-ANTHRACEN
SAUER, J
MIELERT, A
WIEST, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (11): : 3183 - &
[10] DIELS-ALDER REACTIONS 2 - REACTION MECHANISM
SAUER, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) : 16 - +

← 1 2 →