Abstract
The anodic oxidation of substituted [4-hydroxy-3-coumarinyl]-phenylthiomethanes, 1a-1c, in acetonitrile is shown to correspond to a one electron process. The radical cation produced undergoes carbon-sulfur bond fragmentation through loss of a phenylthio radical to give a cation which is trapped by Ritter reaction with acetonitrile to yield the final products 2a-2c in 64-82% yield. In the case of geranyl [4-hydroxy-3-coumarinyl]-phenylthiomethane, Id, the intermediate allylic cation is attacked intramolecularly by a hydroxy nucleophile followed by loss of a proton, to give 2d in 40% yield.
Original language | English (US) |
---|---|
Pages (from-to) | 1773-1778 |
Number of pages | 6 |
Journal | Electrochimica Acta |
Volume | 43 |
Issue number | 12-13 |
DOIs | |
State | Published - May 5 1998 |
Keywords
- Cyclic voltammetry
- Geranyl [4-hydroxy-3-coumarinyl]-phenylthiomethane
- Preparative anodic oxidation
- Reaction mechanism
- Substituted [4-hydroxy-3-coumarinyl]-phenylthiomethanes