1-(o-(Dimethylamino)phenyl)-3-phenylprop-2-en-1-one (62), 3-(o-(dimethylamino)phenyl)-1-phenylpropenone (63) and 1-(o-(dimethyl- amino)phenyl)-3-phenylprop-2-yn-1-one (64) were synthesized and their pyrolytic and photolytic chemistry were studied. Flash vacuum pyrolysis (FVP) of 62 and 64 gave 11H-benzo[a]carbazole (72) and benzo[c]carba-zole (73), FVP of 63 gave phenanthrene (2) and 1-methylquinolin-2(1H)-one (84). Under photolytic conditions, 62 and 64 gave the expected photocyclic products 1-methyl-2-phenylquinolin-4-one (65), while 63 gave the expected photocyclic products (1-methyl-1H-indol-2-yl)phenyl-methanone (66).