Memarian, Hamid Reza; Nasr-Esfahani, Masoud; Boese, Roland; Dopp, Dietrich:

Photoaddition of 2-morpholinoacrylonitrile to substituted 1-acetonaphthones.

In: Liebigs Annalen/Recueil, (1997) ; Nr. 5, S. 1023-1027
Zeitschriftenaufsatz / Fach: Chemie
Acetonaphthones I (R = H, R1 = CN; R = MeO, R1 = H; R = H, R1 = MeO) and 2-morpholinoacrylonitrile undergo [2+2]- or [4+2]-photocycloaddn. depending on the substituents. Thus, I (R = MeO, R1 = H) gave only the [4+2] cycloadduct, but [2+2] cycloadducts were obsd. with I (R = H, R1 = CN; R = H, R1 = MeO). I (R = H, R1 = Br) underwent photosubstitution. The endo or exo orientation of the morpholino group in the cycloadducts was detd. by x-ray crystal structure anal. and NOE expts.