FORCE-FIELD MODELING OF TRANSITION STRUCTURES OF INTRAMOLECULAR ENE REACTIONS AND ABINITIO TRANSITION STRUCTURES FOR AN ACTIVATED ENOPHILE

被引：41

作者：

THOMAS, BE ^{[1
]}

LONCHARICH, RJ ^{[1
]}

HOUK, KN ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 05期

关键词：

D O I：

10.1021/jo00031a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modification of Allinger's MM2 force field has been developed to rationalize and predict the stereochemistries of intramolecular ene reactions. This force field reproduces the stereochemical trends observed for intramolecular ene reactions with unactivated enophiles, but gives poor results with activated enophiles. Ab initio molecular orbital calculations on the ene reaction of acrylonitrile with propene were performed to investigate the change in the transition structure caused by activating substituents.

引用

页码：1354 / 1362

页数：9

共 36 条

[1]

ALDER K, 1962, LIEBIGS ANN CHEM, V651, P141

[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]

ALLINGER NL, 1966, J ORG CHEM, V31, P804

[4]

ALLINGER NL, QCPE395 IND U

[5]

BORTOLUSSI M, 1975, B SOC CHIM FR II-CH, P2731

[6] MODELING OF STERIC CONTROL OF FACIAL STEREOSELECTIVITY - DIELS-ALDER CYCLOADDITIONS OF UNSYMMETRICALLY SUBSTITUTED CYCLOPENTADIENES [J].

BROWN, FK ;

HOUK, KN ;

BURNELL, DJ ;

VALENTA, Z .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3050-3059

[7] TORSIONAL AND STERIC CONTROL OF STEREOSELECTIVITY IN ISODICYCLOPENTADIENE CYCLO-ADDITIONS [J].

BROWN, FK ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :1971-1978

[8]

BURKERT U, 1982, MOL MECHANICS

[9]

Carey FA, 1984, ADV ORGANIC CHEM

[10]

CARRUTHERS W, 1990, CYCLOADDITION REACTI, pCH5

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