Aromatic substitution in the complexes formed upon addition of gaseous arenium ions to proelectrophiles. A FT-ICR study.

被引：13

作者：

Aschi, M ^{[1
]}

Attina, M ^{[1
]}

Cacace, F ^{[1
]}

机构：

[1] UNIV ROMA TOR VERGATA,I-00133 ROME,ITALY

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 1996年 / 22卷 / 07期

关键词：

D O I：

10.1163/156856796X00124

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Experiments based on FT-ICR mass spectrometry provide conclusive evidence for the operation of an alternative mechanism of electrophilic aromatic substitution occurring within the complex formed upon addition of gaseous arenium ions to a variety of proelectrophiles, including alkyl halides, alcohols, epoxides, esters and diazoalkanes. The factors affecting the efficiency of the unconventional substitution are examined in the light of the kinetic results of the FT-ICR experiments.

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页码：645 / 658

页数：14

相关论文

共 15 条

[1] THE CRAFTS-FRIEDEL REACTION - AROMATIC ALKYLATION WITHIN THE COMPLEX FORMED UPON ADDITION OF A GASEOUS ARENIUM ION TO AN OLEFIN [J].

ASCHI, M ;

ATTINA, M ;

CACACE, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1589-1591

[2] An alternative route to electrophilic substitution .2. Aromatic alkylation in the ion neutral complexes formed upon addition of gaseous arenium ions to olefins [J].

Aschi, M ;

Attina, M ;

Cacace, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (51) :12832-12839

[3] EXPERIMENTAL-STUDY ON THE MECHANISM OF GAS-PHASE AROMATIC NITRATION BY PROTONATED METHYL NITRATE [J].

ASCHI, M ;

ATTINA, M ;

CACACE, F ;

RICCI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) :9535-9542

[4] FT-ICR STUDIES OF GAS-PHASE IONIC NITRATION OF BENZENE - THE ROLE OF ELECTRON-TRANSFER AND PROTON-TRANSFER PROCESSES [J].

ATTINA, M ;

CACACE, F ;

SPERANZA, M .

INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES, 1992, 117 (1-3) :37-46

[5]

ATTINA M, 1987, J AM CHEM SOC, V109, P5042

[6] THE RADIOLYTIC APPROACH TO GAS-PHASE ION CHEMISTRY [J].

CACACE, F .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (06) :215-222

[7] IS THE PROTON AFFINITY OF NITRIC-ACID LARGER THAN THE PROTON AFFINITY OF METHYL NITRATE - A DIRECT EXPERIMENTAL ANSWER [J].

CACACE, F ;

ATTINA, M ;

DEPETRIS, G ;

SPERANZA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6413-6417

[8] PROTON AFFINITY OF METHYL NITRATE - LESS THAN PROTON AFFINITY OF NITRIC-ACID [J].

LEE, TJ ;

RICE, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8247-8256

[9]

Lias S.G, 1988, J PHYS CHEM REF DA S, P17

[10]

OLAH GA, 1963, FRIEDELCRAFTS RELATE