Singlet-triplet mechanistic duality in the photosubstitution of nitrophenyl ethers with ethyl glycinate. The role of single electron transfer.

Jorge Marquet, Albert Cantos, Marcial Moreno-Mañas, Eduard Caýon, Iluminada Gallardo

Research output: Contribution to journalArticleResearchpeer-review

10 Citations (Scopus)

Abstract

Mechanistic studies show that 4-nitroveratrole and 4,5-dinitroveratrole undergo nucleophilic aromtic photosubstitution with ethyl glycinate through an SN2Ar* route. However, in the first case the photoreaction takes place through a singlet excited state whereas for 4,5-dinitroanisole a triplet excited state is involved. Electrochemical data for the present photoreactions reagents and for 4-nitroanisole, involved in a related photoreaction previously described by us, are reported. A mechanistic scheme, governed by a direct collapse - electron transfer competition in the singlet excited state stage, is proposed for the nucleophilic aromatic photosubstitution reactions of nitrophenyl ethers with amine nucleophiles. © 1992.
Original languageEnglish
Pages (from-to)1333-1342
JournalTetrahedron
Volume48
Issue number7
DOIs
Publication statusPublished - 1 Jan 1992

Keywords

  • Mechanisms
  • Nitrophenyl Ethers
  • Photosubstitution
  • Redox Potentials
  • Single Electron Transfer

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