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Regioselectivity of the electrophilic nitration of α, α, α-trihalomethoxybenzenes

La regioselettività della nitrazione elettrofila degli α, α, α-trialogenometossibenzeni

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Nitration of α, α, α-trihalomethoxybenzenes with nitronium tetrafluoroborate or methyl nitrate/boron trifluoride in nitromethane solution was studied and compared to that of halobenzenes. Predominantpara-substitution is observed with no formation ofmeta isomer. The substrate reactivity compared to benzene (determined in competition experiments) is 0.1 to 0.3.


La nitrazione degli α, α, α-trialogenometossibenzeni con nitronio tetra-fluoroborato o nitrato di metile/trifluoruro di boro in nitrometano è stata studiata e paragonata a quella degli alogenobenzeni. È stata osservata principalmente la para-sostituzione, senza formazione delľisomero meta. La reattività dei substrati relativa alla reattività del benzene è k(C6H5OCX3)/k(C6H6) = 0.1-0.3.

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Correspondence to Nota di George A. Olah or Takehiko Yamato or Nirupam Trivedi or Akihiko Tsuge or Judith A. Olah.

Additional information

Nella seduta del 21 aprile 1990.

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Olah, N.d.G.A., Yamato, T., Trivedi, N. et al. Regioselectivity of the electrophilic nitration of α, α, α-trihalomethoxybenzenes. Rend. Fis. Acc. Lincei 1, 307–311 (1990). https://doi.org/10.1007/BF03001765

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Key words

  • Nitration
  • Aromatic Substitution
  • Substituent Effect