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Wurtz Coupling: By far, not the worst coupling

LJ

Laura Johnson

Transcript

Wurtz Coupling: By far, not the worst coupling

Uses

Wurtz-Fittig Reaction

Limitations

  • alkyl+aryl halides
  • necessary to have reactivity difference
  • expands reaction utility
  • yields vary based on reactants (12-54%)
  • extremely reactive
  • intolerant of some functional groups
  • alkane mixtures form a multitude of difficult to separate products
  • solvent restrictions
  • bulky alkanes can result in alkene product
  • yields vary widely based on reactants (37-92%)

Mechanism

Recent Intriguing Application

Polymers and Nano materials such as graphene

Other Modifications

Wurtz Reaction (1855)

uses in water filtration, and creation of extremely strong, well conducting materials,

  • heterolytic bond cleavage
  • radical formation
  • nucleophilic substitution reaction
  • Coupling to form large dimers
  • Polymer synthesis
  • Macro-cyclization
  • Strained ring structures
  • Solubilizing the Na with tetraphenyl ethylene (Müller Modification)
  • Use of other metals, suppress side reactions, improve yields ( Cu, Mn₂(CO)₁₀, Li, Na(Hg), Na-K alloy, Zn)
  • two equivalence of identical alkyl or benzyl halides
  • reactive metal : Na for traditional Wurtz
  • carbon-carbon bond formation

Charles-Adolphe Wurtz

Features of Wurtz Coupling

References

  • Heterogeneous Reaction
  • Primary alkyl iodides best substrate
  • Secondary halides poor substrate
  • French chemist
  • Assisted reform of chemical theory
  • Worked under Jean Baptiste Dumas
  • Discovered Aldol Reaction
  • Name immortalized on Eiffel Tower
  • Trained Crafts, Fittig, Freidel, Combes and van't Hoff
  • World's most impressive mutton chops

http://en.wikipedia.org/wiki/Wurtz_reaction

http://www.organic-chemistry.org/namedreactions/wurtz-reaction.shtm

http://www.organic-chemistry.org/namedreactions/wurtz-fittig-reaction.shtm

http://www.chem.ucla.edu/harding/IGOC/W/wurtz_reaction.html

http://www.name-reaction.com/wurtz-reaction

Strategic Applications of Named Reactions in Organic Synthesis By Laszlo Kurti, Barbara Czako

The application of the wurtz reaction to the synthesis of polymers of the polyxylylene type—II. The properties of the polycondensation products of bis-chloromethyl derivatives of aromatic hydrocarbons and metallic sodium E.P. Mel'nikova, A.A. Vansheidt, M.G. Krakovyak, L.V. Kukhareva

http://arunsharmachemistry2013.blogspot.com/2013/06/wurtz-reaction.html

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