Photosubstitution-photoreduction mechanistic duality in the SET photoreactions of nitrophenyl ethers with amines. The role of the steps that follow the ET

Miquel Mir, Jordi Marquet, Oriol Massot

Research output: Contribution to journalArticleResearchpeer-review

7 Citations (Scopus)

Abstract

Nitrophenyl ethers are photoreduced by primary amines in water through a mechanism initiated by single electron transfer that is in direct competition with the single electron transfer photosubstitution mechanism (S(N)Ar*-SET). Our results indicate that the preferred pathway does not depend on the electron donor or proton donor ability of the amine. The key factor that determines the progress of the photoreaction is the structure of the carbon skeleton of the amine, particularly the type of hydrogens on the carbon α to the amino group. A mechanistic rationale that includes hydrogen atom transfer as a key step is discussed.
Original languageEnglish
Pages (from-to)12603-12614
JournalTetrahedron
Volume55
Issue number43
DOIs
Publication statusPublished - 22 Oct 1999

Keywords

  • Electron transfer
  • Nitro compounds
  • Photochemistry
  • Reduction

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