104228-25-3Relevant academic research and scientific papers
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 (1984)
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.
Methanol-Incorporated Photoaddition of N-Methyl-1,2-naphthalenedicarboximide with Alkenes and Dienes
Kubo, Yasuo,Mihara, Mariko,Araki, Takeo
, p. 241 - 248 (1987)
Irradiation of acetonitrile-methanol solutions of N-methyl-1,2-naphthalenedicarboximide (1b) with 1,1-diphenylethylene gave a methanol-incorporated adduct at a carbonyl carbon atom in 1b together with 2,2-diphenylethyl methyl ether as a typical electron-transfer photosensitized product.The photoreaction of 1b with α-methylstyrene, styrene (2c), or 2-methyl-2-butene in the same solvent system gave a regio-isomeric pair of a mixture of two diastereomers of methanol-incorporated adducts at carbonyl atoms.The irradiation of 1b with 2,3-dimethyl-2-butene and ethyl vinyl ether (2h) in benzene-methanol afforded methanol- incorporated adducts, although no reaction was observed for irradiation in acetonitrile-methanol.The irradiation of 1b with 2,5-dimethyl-2,4-hexadiene in acetonitrile-methanol also resulted in the formation of methanol-incorporated adducts.The values of the free-energy change associated with an electron-transfer (ΔGet) from the alkenes to the singlet excited state of 1b and fluorescence quenching rate constants support the photochemical single-electron-transfer mechanism for the addition.A preferential addition at the carbonyl carbon atom in 1b as well as that at the more sterically hindered carbonyl carbon atom in the reaction of 1b with 2c and 2h is explainable on the basis of the spin densities of the radical anion of 1b derived by a photochemical single-electron-transfer.
Photochemical Reactions of N-Methyl-1,2-naphthalenedicarboximide with Alkenes. Preferential Naphthazepinedione Formation
Kubo, Yasuo,Toda, Rie,Yamane, Kengo,Araki, Takeo
, p. 191 - 200 (2007/10/02)
Irradiation of benzene solutions of N-methyl-1,2-naphthalenedicarboximide (1) in the presence of alkenes (2a,b,d-i) gave two regio-isomers of naphthazepinediones (3a,b,d-i and 4a,b,d-i).Stereospecificity of the naphthazepinedione formation was observed in the reaction with cis- and trans-2-butene (2a and 2b).Naphthazepinediones (3j and 4j) produced by the irradiation of 1 with ethyl vinyl ether (2j) underwent secondary photoreactions to give 7 and 8, respectively.On the other hand, irradiation of 1 with 2,3-dimethyl-2-butene (2k) resulted in the formation of oxetanes (13a,b) and 1:1-adducts of 1 and 2k at the carbonyl groups of 1 (14 and 15,ab).Irradiation of 1 with cis-stilbene (2l) afforded oxetanes (22a,b) and fragmentation products of oxetanes (23a,b, and 24).Stern-Volmer slopes (kqτ) obtained from quenching of fluorescence of 1 by alkenes (2a-e,k) correlated to some extent with relative rates for disappearance of 1 in the reaction.Preferential formation of the naphthazepinedione was rationalized by the nature of the excited singlet state of 1 compared with those of other N-methylarenedicarboximides.
