AbstractPhenanthrenequinone (1) reacts with 1‐dialkylamino‐1‐alkynes2via(2 + 2)‐cyclo‐addition to γ‐oxo‐α,β‐unsatutrated amides3Eof the quinone methide type.These adducts isomerise under the influence of base to α,β‐unsaturated hydroxyamides4. Irradiation of the adducts3Ein benzene affords the same α,β‐unsaturated hydroxyamides4viaintramolecular hydrogen‐abstraction.Treatment of3Ewith boron trifluoride gives 3‐alkyl‐3‐dialkylamino‐2,3‐dihydrophenanthro[9,10‐b]furan‐2‐ones6in good yields. With hydrochloric acid in acetic acid, the unsaturated hydroxyamides 4 afford 3‐alkylidene‐2,3‐dihydrophenanthro[9,10‐b]furan‐2‐ones 7. Similar reactions have been