Perfluoralkylsubstituierte β-Chlorvinylaldehyde: eine neue Klasse von building blocks zur Synthese fluorierter Heterocyclen

Fluorinated Five‐Membered Nitrogen‐Containing Heterocycles

“…Greif and coworkers developed perfluoroalkyl-substituted b-chlorovinylaldehydes as new building blocks for a number of fluorinated heterocyclic systems such as thiazoles, pyridines, pyrazoles, and benzimidazoles. 166 oalkyl-5-aryl-1,2,3 triazoles. Electrocyclic ring closure of an initially formed azido vinyladehyde followed by loss of "CO" explains the formation of the triazoles (Fig.…”

Fluorine-containing alkyl(aryl) vinyl sulfides

“…Successive treatment of 3-chloro-2-phenyl-3-trifluoromethylacrolein with sodium sulfide and benzyl bromide yields vinyl sulfide 24 resulting from substitution of the benzylthio group for the chlorine atom. 58 1-Chloro-2,2-dicyano-1-polyfluoroalkylethylenes react with thiols on heating in the absence of bases. The reaction can be followed by monitoring the evolution of hydrogen chloride.…”

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

“…Compound 149 simply undergoes an electrocyclic closure to a 5-membered ring, which then undergoes nucleophilic attack of the aldehyde by H 2 O to deformylate the cyclic intermediate. The mechanism of the reaction is shown in Scheme 24 [139].…”