Under the influence of strong bases in dimethyl sulfoxide (DMSO) under mild conditions, carbazole and indole add smoothly to phenylacetylene to give cis isomers of 9-(2-phenylvinyl)carbazole and 1-(2-phenylvinyl)indole. A cis-phenyl group markedly reduces the activity of the double bond of phenylvinylcarbazole in acid hydrolysis, but, as in the case of other alkenylcarbazoles, protonation takes place at the vinyl Cβ atom. It was established by 13C NMR and UV spectroscopy that the carbazolyl group displays π-donor properties with respect to the styryl group.
ASJC Scopus subject areas
- Organic Chemistry