The reaction of ortho-(cyclohex-2-enyl)aniline with I-2 in nonpolar and pol
ar solvents affords predominantly 1-iodohexahydrocarbazole and azatricyclot
ridecatriene, respectively. Under analogous conditions, 4-methyl-2-(1-methy
lbut-2-en-1-yl)aniline undergoes cyclization to form exclusively products w
ith quinoline structures regardless of the Solvent used.