Comparison of reactivities of 1- and 4-oxotetrahydrocarbazoles in reactions with nucleophilic and electrophilic reagents

Article abstract of DOI:10.1007/s11172-006-0054-0

The half-wave potentials of polarographic reduction of the carbonyl group in unsubstituted and N-methyl- and N-phenylsulfonyl-substituted 1- and 4-oxotetrahydrocarbazoles and their reactivities in reactions with nucleophilic (NaBH₄, malonodinitrile, and cyanoacetamide) and electrophilic (DMF dimethyl acetal) reagents were compared. 4-Oxotetrahydrocarbazoles are much less reactive than 1-oxotetrahydrocarbazoles.