Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole
| Authors | |
|---|---|
| Year of publication | 2002 |
| Type | Article in Periodical |
| Magazine / Source | Photochemical and Photobiological Sciences |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | microwave; photochemistry |
| Description | A temperature-sensitive photochemical nucleophilic aromatic substitution on 4-nitroanisole by the hydroxide ion in homogeneous solutions, in a two-phase system under phase-transfer catalysis conditions, and in the microwave field is reported. It was found that reaction regioselectivity dramatically changes with temperature in the region of -20 to 196 oC. The quantum yield of the 4-methoxyphenol formation was found to be temperature independent, in contrast to that of the 4-nitrophenol formation, suggesting that there is a temperature dependent process occurring after the partitioning between replacement of the nitro group and the methoxy group has taken place. The reaction was also investigated by the quantum chemical calculations. A technique for microwave-assisted photochemical synthesis is proposed as an efficient and practical tool for organic synthesis |
| Related projects: |