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Phenyl cyclopropyl ether in electrophilic substitution reactions

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Conclusions

  1. 1.

    The three-membered ring of cyclopropyl phenyl ether is stable in halogenation and acylation reactions, while the cyclopropoxy group exhibits a para-orienting effect.

  2. 2.

    The nitration of cyclopropyl phenyl ether with dilute HNO3 solution is accompanied by a cleavage of the three-membered ring, with the formation of 2,4-dinitrophenol and propionaldehyde.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1778–1782, August, 1972.

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Petinskii, A.A., Shostakovskii, S.M. & Kositsyna, É.I. Phenyl cyclopropyl ether in electrophilic substitution reactions. Russ Chem Bull 21, 1720–1723 (1972). https://doi.org/10.1007/BF00851187

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Keywords

  • Ether
  • Propionaldehyde
  • Phenyl
  • HNO3
  • Halogenation