99033-60-0Relevant academic research and scientific papers
1,4-Photoadditions of α-Morpholinoacrylonitrile to 1-Acylnaphthalenes
Doepp, Dietrich,Memarian, Hamid Reza
, p. 315 - 319 (2007/10/02)
Photoexcited 1-naphthaldehyde (1a), 1-acetonaphthone (1b), and 1-naphthophenone (1c) add α-morpholinoacrylonitrile (2a) in a mode with exceptional regio- and stereoselective formation of only one diastereomer of the two possible regioisomeric 1,4-dihydro-1,4-ethanonaphthalene adducts.An independently formed 1,2-adduct 4 was detected and isolated in very low yield. 4 is thermally and photochemically (313-nm excitation) cleaved into the starting materials with no indication of direct interconversion into 3b.Compound 3b is stable towards 313-nm radiation, but is efficiently isomerized to give the dihydrobenzosemibullvalene 7 upon 254-nm excitation. - All observations point to the first excited triplet state as the starting point for the 1,4-additions.
