1. 3‐Trifloxy‐3‐(trifluoromethyl)prop‐2‐ene 1‐Iminium Salts as Precursors for Elusive 3‐(Trifluoromethyl)prop‐2‐yne 1‐Iminium Salts
- Author
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Gerhard Maas, Angelika Freytag, Michael Keim, and Katharina Konetzke
- Subjects
DDC 540 / Chemistry & allied sciences ,Trifluoromethyl ,Organic Chemistry ,Triazole ,Iminium ,Organofluorine chemistry ,Cycloaddition ,Ring formation (Chemistry) ,Alkine ,chemistry.chemical_compound ,chemistry ,Alkynes ,ddc:540 ,Organofluorine compounds ,1,2,3-Triazoles ,Organic chemistry ,Fluororganische Verbindungen ,Azide ,Iminium Salts ,Physical and Theoretical Chemistry ,Ene reaction ,Diels–Alder reaction - 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. 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., publishedVersion
- Published
- 2021