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

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.

Automated summary

3-(Trifluoromethyl)prop-2-yne 1-iminium triflate salts were synthesized by elimination of triflic acid, and exhibited excellent reactivity in various cycloaddition reactions.