Obtention de 3-F-alkyl-4-ethoxycarbonyl furanes

Synthesis of fluorofurans and perfluoroalkylfurans

“…Furan can easily react with fluoroalkyl derivatives of acetylenes as heterodiene [92][93][94][95][96]. Intermediate 7-oxa-[2.2.1]-bicyclo-2,5-dienes afford b-trifluoromethylfurans upon hydrogenation and consequent pyrolysis (Scheme 44) [92,[95][96][97][98][99][100] or via reaction with 2,3,4,5-tetraphenylcyclopentadienone (Scheme 45) [93,94].…”

“…Intermediate 7-oxa-[2.2.1]-bicyclo-2,5-dienes afford b-trifluoromethylfurans upon hydrogenation and consequent pyrolysis (Scheme 44) [92,[95][96][97][98][99][100] or via reaction with 2,3,4,5-tetraphenylcyclopentadienone (Scheme 45) [93,94]. This method allows to obtain furans with various perfluoroalkyl groups in one or two positions of the furan ring.…”

Synthesis of heterocycles with polyfluoroalkyl substituents from unsaturated compounds containing polyfluoroalkyl groups. (Review)

“…Diels-Alder reaction of ethyl polyfluoroalkylacetylenecarboxylates with the N-pyrrolecarboxylate ester 143[103] or furan 144[103,104] it is possible to synthesize new derivatives of the above-mentioned heterocycles with polyfluoroalkyl substituents 145 and 146 through intermediate compounds 147 and 148.…”

“…Thus, methyl vinyl ketone and substituted trifluoropropynylamine 139 form the adduct 140 (yield 97%) as a result of [4+2] cycloaddition[102].Perfluoroalkylacetylenes react with substituted furans, giving the Diels-Alder products 141, the action of heat on which leads to the substituted oxepins 142 as a result of a thermal retro-Diels-Alder reaction[103][104][105][106][107][108][109][110].…”

Recent trends in the Chemistry of fluorinated five and six‐membered heterocycles

“…Perfluoroalkyl-substituted acetylenes, such as 197 react with furans 196 to give the Diels-Alder adducts 198. The latter undergo thermal retro-Diels-Alder reaction to give the 3-trifluoromethylfuran 200 in a high yield (Scheme 30) [169][170][171][172][173][174][175][176].…”