106344-70-1Relevant articles and documents
Photochemical Reaction of N-Methylnaphthalene-1,8-dicarboximide with Alkenes, Dienes, and Furans. Cyclobutane and Oxetane Formation
Kubo, Yasuo,Suto, Manami,Tojo, Sachiko,Araki, Takeo
, p. 771 - 780 (2007/10/02)
Irradiation of benzene solutions of N-methylnaphthalene-1,8-dicarboximide (1) in the presence of alkenes (2b-k) and dienes (9a-c) give the cyclobutanes (3b-j), (4c,e,f,h,i), and (10a-c).Stereospecifity of cyclobutane formation was observer in the reaction with cis- and trans-but-2-ene (2h,i), and some endo-selectivity was observed in the reaction with styrene (2f).In contrast, irradiation of benzene solutions of (1) in the prasence of trans- and cis-stilbene (2j,k), 2,5-dimethylbuta-2,4-diene (9d), and furans (14a,b) gave the fragmentation products (7a,b), (8), (13a,b), (16a,b), and (17a,b) arising via precursor oxetanes.In fluorescence quenching studies of the alkenes (2a-d) a linear relationship was found for log plots of their Stern-Volmer slopes (κqτ) and ionization potentials, and the furans (14a) and (9d) showed new emissions, possibly from exciplexes.A tentative mechanistic scheme for the two types of reactions involving two types of exciplexes generated by the reaction of the singlet excited state of (1) and unsaturated compounds is proposed.
