three memebered ring

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  • Created by: S
  • Created on: 26-03-17 19:33
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  • Three Membered ring-kinetically favoured but thermodynamically disfavoured
    • Epoxide
      • Electron rich Alkene + mCPBA
      • Electron poor Alkene +NaOH/H202
      • Alkene + Br,H2o->HO-Br (halohydrin)
        • K2O3 used to convert it into an epoxide
      • Darzens Reaction ( alpha -chloro eter aldol reaction)
      • Ketone/aldehyde +Me3S+I- +base
    • Aziridines- similar to epoxide but less reactive to nucleophile than epoxide usully requires activation by protonation
      • Alkene
        • R-Br->R-N3(NaN3 SN2) thermol decomposition of azides  to form nitrenes which would react to alkene to form aziridines
    • Cyclopropane
      • prepared from 4 halo bromide with NaOH
        • 4 halo bromide can be synthesised via ketoester,NaOEt and epoxide then HBr and H20(-CO2)
      • Alkenes and carbenes
        • Carbenes
          • CH2I2 + Zn ->H2C:
          • Diazo compounds can undergo thermal composition to from carbenes

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