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FURAN

FURAN. The least aromatic 5-membered ring. Reaction with electrophiles - Protonation. Conc. H 2 SO 4 Lewis acids (i.e. AlCl 3 ). Decomp. Reaction with electrophiles - Nitration. Cannot use conc. HNO 3 / H 2 SO 4. Halogenation. Reaction with electrophiles - Acylation. Alkylation.

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FURAN

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  1. FURAN The least aromatic 5-membered ring Reaction with electrophiles - Protonation Conc. H2SO4 Lewis acids (i.e. AlCl3) Decomp.

  2. Reaction with electrophiles - Nitration Cannot use conc. HNO3 / H2SO4 Halogenation

  3. Reaction with electrophiles - Acylation Alkylation Generally not practical (polyalkylation, polymerisation) Condensation with Aldehydes and Ketones C.f.

  4. Reaction with electrophiles - Condensation with imines / iminium ions Reaction with oxidating agents Reaction with nucleophiles Some ex. on furans activated with -NO2 group

  5. Metallation and further react.

  6. Pd-cat couplings Heteroaryl-Heck c.f.

  7. Cycloadditions Furanes as diene - one of the first DA examples Furan reacts with many dienophiles (alkenes, alkynes, allenes) exo isolated (termodyn favoured) endo (kinetic prod.) With 1O2 Furan as dienophile (only intramolec. ex) Photochemical cycloaddition

  8. Furyl-CH2-X Aminofurans -Aminoform -Unstable Oxyfurans Isol. marine sponges cytotoxic

  9. Synthesis of Furans Carbonyl condensations Strategy a - pyrroles Paal Knorr Strategy a1 Paal Knorr (1,4-dikacarbonyl)

  10. Strategy b

  11. Pd-cat. Cyclisations etc.

  12. Cycloadditions

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