The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4gave N-chlorocarbazole in 63-95% yield. It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole. These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction. In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed. No evidence for an intramolecular rearrangement was found.
All Science Journal Classification (ASJC) codes
- Organic Chemistry