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 language | English |
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Pages (from-to) | 1333-1342 |
Journal | Tetrahedron |
Volume | 48 |
Issue number | 7 |
DOIs | |
Publication status | Published - 1 Jan 1992 |
Keywords
- Mechanisms
- Nitrophenyl Ethers
- Photosubstitution
- Redox Potentials
- Single Electron Transfer