Unusual transformation of a fluoroalkyl-containing β-aminovinyl ketone

Russian Chemical Bulletin -     

Reactions of regioisomeric fluoroalkyl-containing β-aminovinyl ketones with hydrazines

Fluoroalkyl -alkyl--aminovinyl ketones react with hydrazine hydrate to give the respective razoles and with phenylhydrazine they form a mixture of pyrazoles and 5 hydroxy-²-pyrazolines. Alkyl(aryl) -fluoroalkyl--aminovinylketones do not react with the hydrazines mentioned above. With 2,4-dinitrophenylhydrazine, both types of fluoroalkyl-containing -aminovinyl ketones give only hydrazones of the corresponding methyl alkyl(aryl) ketones.     

Synthesis of polyfluorinated ketonesvia the ate-complexes

Russian Chemical Bulletin - Asymmetric polyfluorinated ketones RFCOR are formed by treating various derivatives of (polyfluoro)alkanoic acids (esters, anhydrides, acid chlorides) with lithium...     

Stereoisomerism ofβ-polyfluoroalkyl-α,β-enones

-Polyfluoroalkyl-,-enones formed in the E,Z form are converted by the action of atmospheric oxygen into a 937 mixture of E,Z and Z,E isomers in the dark and 6040 mixture of these isomers in the light. The Z isomer of 1-phenyl-4,4, 4-trifluoro-2-buten-1-one was isolated preparatively for the first time and its E conformation relative to the C-C bond was established. The Z,E isomer spontaneously transforms into the indicated equilibrium mixtures.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1685–1689, July, 1991.     

Bromination of regioisomeric fluorine-containing β-aminovinyl ketones

Bromination of -aminovinyl ketones (AVK) with geminal arrangement of the fluoroalkyl and amino groups gives N-bromo derivatives. Regioisomeric AVK with the amino groups in the -position relative to the fluoroalkyl group undergo bromination under analogous conditions to give a mixture of the -bromo and ,N-dibromo derivatives. -Bromo derivatives of AVK disproportionate upon storage.Division of Fine Chemical Synthesis, Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, 620219 Ekaterinburg. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 746–749, March, 1992.     

A new synthesis of 4′-trifluoromethyl-2,2′:6′,2″-terpyridine

1. Download : Download high-res image (44KB)
2. Download : Download full-size image

     

Perfluoro(1,2-epoxycyclohexane) in the synthesis of fluorinated heterocycles

Perfluoro(1,2-epoxycyclohexane) readily reacts with bifunctional nucleophiles (urea, thiourea, and benzene-1,2-diamine) via opening of the oxirane ring and subsequent heterocyclization to give fluorinated benzimidazole, 1,3-benzothiazole, and phenazine derivatives, respectively.     

Bis(acetylaryl) podands in the synthesis of fluorine-containing bis(β-diketones) joined by a polyether spacer

O-Alkylation of 2-acetylphenols with α,ω-dichloro derivatives of oligoethylene glycols in the presence of KOH and Al₂O₃ in DMF gave the corresponding podands. Their condensation with ethyl trifluoroacetate afforded fluorine-containing bis(β-diketones) with the aryl fragments linked by conformationally flexible polyether spacers.     

Synthesis and structure of fluoroalkyl containing lithium 1,3-diketonates

Russian Journal of General Chemistry - Methods of synthesis and IR, mass, NMR 1H, 19F, 13C spectra as well as X-ray analysis of fluoroalkyl containing lithium 1,3-diketonates are reviewed.