AbstractThe indolo‐2,3‐quinodimethane (5), generated from 2,3‐bis(bromomethyl)indole (4), was trapped with unsymmetrical carbodienophiles or N, N′‐p‐phenylenedimaleimide to furnish the 1,2,3,4‐tetrahydrocarbazoles (6–9). [4 + 2]‐Cycloaddition of5with tetracyanoethylene gave rise to the tetracyanocarbazole (10) and a subsequent product11aor11b. The Diels‐Alder reaction of5with divinyl sulfone was regiospecific within the detection limits of HPLC analysis. Similarly, the reaction of5with N, N′‐p‐phenylenedimaleimide yielded