3-Trifloxy-3-(trifluoromethyl)prop-2-ene 1-Iminium Salts as Precursors for Elusive 3-(Trifluoromethyl)prop-2-yne 1-Iminium Salts

被引：2

作者：

Keim, Michael ^{[1
]}

Konetzke, Katharina ^{[1
]}

Freytag, Angelika ^{[1
]}

Maas, Gerhard ^{[1
]}

机构：

[1] Ulm Univ, Inst Organ Chem 1, Albert Einstein Allee 11, D-89081 Ulm, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 23期

关键词：

Alkynes; Cycloaddition; Iminium Salts; Organofluorine Compounds; 1; 2; 3-Triazoles; DIELS-ALDER REACTION; EFFICIENT SYNTHESIS; ORGANOFLUORINE CHEMISTRY; REGIOSPECIFIC SYNTHESIS; CYCLOADDITION REACTIONS; FLUORINE; TRIAZOLE; KETONES; AZIDE;

D O I：

10.1002/ejoc.202100567

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Abstract: 3-(Trifluoromethyl)prop-2-yne 1-iminium triflate salts were generated from 3-trifloxy-3-(trifluoromethyl)prop-2-ene 1-iminium salts by triethylamine-assisted elimination of triflic acid and trapped in situ in various cycloaddition reactions. These included Diels-Alder reactions with 1,3-dienes, [2+2] cycloaddition with 1,4-diphenylbuta-1,3-diene, and [3+2] cycloaddition with organoazides. All these reactions revealed the excellent dienophilic and dipolarophilic reactivity of the electrophilic C,C triple bond of the novel 3-CF3-propyniminium salts.

引用

页码：3426 / 3441

页数：16

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