A synthesis of trifluoromethyl-substituted naphthalenes

Mellor, John M.; El‐Sagheer, Afaf H.; Salem, Ezz El-Din M

doi:10.1016/s0040-4039(00)01254-5

Cited by 14 publications

(1 citation statement)

References 9 publications

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“…[30,31]). Because of the expected destabilizing effect of strongly electron attracting perfluoroalkyl groups on the intermediate carbocation, our work may be of general interest to organic chemists.…”

Section: Introductionmentioning

confidence: 99%

Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols

et al. 2011

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(Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformation, giving an 89% yield of isomeric product mixture, was P2O5 in benzene at 80-90 °C. Products were characterized on the basis of their mass spectra and retention time information, and some peaks in the mass spectra were identified from their molecular fragments. Structures were assigned to the three most abundant products of (perfluorohexyl)tetramethylcyclopentenol dehydration. Formal dehydration kinetics showed a second order reaction in benzene but zeroth order with induction period in chlorobenzene, suggesting mass transfer limitations in the more polar chlorobenzene. Some of the products were formed by consecutive isomerization of the others, as shown by the kinetic analysis.

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Section: Introductionmentioning

confidence: 99%

Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols

et al. 2011

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CF₃‐substituierte aromatische und heterocyclische Bausteine

Schlosser

2006

Angewandte Chemie

185

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Fluor bleibt ein Geheimtipp in den Lebenswissenschaften, da sich mit diesem Element biologische Eigenschaften abstimmen lassen. Die Synthese fluorhaltiger Zielverbindungen ist jedoch nicht immer einfach: Praktisch jedes Fluor‐Atom, das an ein organisches Gerüst angeheftet wird, muss letztlich einer anorganischen Quelle entnommen werden. Ausschlaggebend für die Syntheseplanung ist die Entscheidung, auf welcher Stufe und wie das Halogen eingeführt werden soll. Gängige technische Verfahren, insbesondere die Verdrängung von Chlor mit wasserfreiem Fluorwasserstoff oder mit Kaliumfluorid, lassen sich schwerlich zweckmäßig im Labormaßstab ausführen. Allgemeingültige Methoden für Industrie wie Hochschulbereich finden deshalb großen Anklang. Für die Synthese CF3‐substituierter Arene oder Heterocyclen gibt es zwei hervorragende Möglichkeiten: Die CF3‐Gruppe kann paketweise durch Kupplung eines geeigneten Substrats mit in situ erzeugtem (Trifluormethyl)kupfer übertragen werden, oder man kann von einem CF3‐haltigen Aren oder Heterocyclus als Grundgerüst ausgehen und dieses mit den noch fehlenden Teilen vervollständigen.

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CF₃‐Bearing Aromatic and Heterocyclic Building Blocks

2006

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Fluorine remains an insiders' tip in the life sciences as it enables the fine-tuning of biological properties. However, the synthesis of fluorine-substituted target compounds is not always trivial. Virtually any fluorine atom attached to an organic backbone has ultimately to be imported from inorganic sources. Crucial for the entire synthetic planning in medicinal and agricultural research is the decision on at what stage and how the halogen will be introduced. Standard technical processes, in particular the displacement of chlorine using anhydrous hydrogen fluoride or potassium fluoride, can hardly be implemented rationally on the laboratory scale. Universal methods that are applicable by both industrial and academic researchers thus have great appeal. If a trifluoromethyl-substituted arene or heterocycle is the target compound, two splendid options exist. The CF(3) group can be delivered packagewise by coupling an appropriate substrate with in situ generated (trifluoromethyl)copper. Alternatively, one may start from a CF(3)-substituted arene or heterocycle as a core and complete it with the missing parts of the ultimate structure.

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A synthesis of trifluoromethyl-substituted naphthalenes

Cited by 14 publications

References 9 publications

Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols

Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols

CF₃‐substituierte aromatische und heterocyclische Bausteine

CF₃‐Bearing Aromatic and Heterocyclic Building Blocks

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A synthesis of trifluoromethyl-substituted naphthalenes

Cited by 14 publications

References 9 publications

Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols

Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols

CF3‐substituierte aromatische und heterocyclische Bausteine

CF3‐Bearing Aromatic and Heterocyclic Building Blocks

Contact Info

Product

Resources

About

CF₃‐substituierte aromatische und heterocyclische Bausteine

CF₃‐Bearing Aromatic and Heterocyclic Building Blocks