106344-60-9Relevant academic research and scientific papers
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.
PHOTOCHEMICAL REACTIONS OF NAPHTHALENEDICARBOXIMIDES. EFFECT OF ARENE STRUCTURE IN IMIDE COMPOUNDS ON REACTION WITH OLEFINS
Kubo, Yasuo,Tojo, Sachiko,Suto, Manami,Toda, Rie,Araki, Takeo
, p. 2075 - 2078 (2007/10/02)
Photolyses of N-methylnaphthalenedicarboximides (1,8-NI, 2,3-NI, and 1,2-NI) with various olefins were investigated in benzene.The reaction pathways depended largely on the structure of arene moiety of the imides.The main reactions of 1,8-NI, 2,3-NI, and 1,2-NI were found as cyclobutane formation, oxetane formation, and insertion of olefin between the C(=O)-N bond of imide moiety, respectively.
