- Independent Generation and Reactivity of 2′-Deoxyguanosin- N1-yl Radical
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2′-Deoxyguanosin-N1-yl radical (dG(N1-H)?) is the thermodynamically favored one-electron oxidation product of 2′-deoxyguanosine (dG), the most readily oxidized native nucleoside. dG(N1-H)? is produced by the formal dehydration of a hydroxyl radical adduct of dG as well as by deprotonation of the corresponding radical cation. dG(N1-H)? were formed as a result of the indirect and direct effects of ionizing radiation, among other DNA damaging agents. dG(N1-H)? was generated photochemically (λmax = 350 nm) from an N-aryloxy-naphthalimide precursor (3). The quantum yield for photochemical conversion of 3 is ~0.03 and decreases significantly in the presence O2, suggesting that bond scission occurs from a triplet excited state. dG is formed quantitatively in the presence of excess β-mercaptoethanol. In the absence of a reducing agent, dG(N1-H)? oxidizes 3, decreasing the dG yield to ~50%. Addition of 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodGuo) as a sacrificial reductant results in a quantitative yield of dG and two-electron oxidation products of 8-oxodGuo. N-Aryloxy-naphthalimide 3 is an efficient and high-yielding photochemical precursor of dG(N1-H)? that will facilitate mechanistic studies on the reactivity of this important reactive intermediate involved in DNA damage.
- Zheng, Liwei,Greenberg, Marc M.
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- Synthesis and fluorescence study of naphthalimide-coumarin, naphthalimide-luminol conjugates
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Fluorescent naphthalimide-coumarin and naphthalimide-luminol conjugates were prepared by nucleophilic substitution reaction. The synthesized conjugates were characterized by 1H-NMR, 13C-NMR, mass and IR spectra. The absorption and fluorescence of these conjugates revealed that naphthalimide-luminol conjugates are more fluorescent than the naphthalimide-coumarin conjugates. In proton accepting DMSO solvent the fluorescence of the conjugates was quenched, while in proton donating ethanol solvent enhanced fluorescence was noticed. Based on the excitation maxima and fluorescence maxima it was found that in naphthalimide-coumarin conjugates coumarin acting as donor and naphthalimide acting as acceptor where as in naphthalimide-luminol conjugates naphthalimide acts as donor and luminol acts as acceptor.
- Sheshashena Reddy,Ram Reddy
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- Novel chiral naphthalimide-cycloalkanediamine conjugates: Design, synthesis and antitumor activity
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A novel series of enantiopure naphthalimide-cycloalkanediamine conjugates were designed, synthetized and evaluated for in vitro cytotoxicity against human colon adenocarcinoma (LoVo), human lung adenocarcinoma (A549), human cervical carcinoma (Hela) and human promyelocytic leukemia cell lines (HL-60). The cytotoxicity of the compounds was highly dependent on size and relative stereochemistry of the cycloalkyl ring as well as length of the spacer. By contrast, any kind of enantioselection was observed for each pair of enantiomers. Flow cytometric analysis indicated that compounds 22 and 23 could effectively induce G2/M arrest in the four previous cell lines despite a mild apoptotic effect.
- Costales, Paula,Ríos-Lombardía, Nicolás,Lorenzo-Herrero, Seila,Morís, Francisco,González-Sabín, Javier
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- Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea
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N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.
- Liu, Luxiao,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
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p. 1351 - 1357
(2019/11/19)
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- Cytotoxicity, anticancer, and antioxidant properties of mono and bis-naphthalimido β-lactam conjugates
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This article reports the diastereoselective synthesis of some novel naphthalimido and bis-naphthalimido β-lactam derivatives and a preliminary evaluation of their anticancer properties. The reactions were completely diastereoselective, leading exclusively to the formation of cis-β-lactams 11a–l and trans-bis-β-lactams 16a–g. All of these compounds were obtained in good to excellent yields and their structures were established based on IR, 1H NMR, 13C NMR spectral data, and elemental analysis. Each of the β-lactams was screened for antioxidant and anticancer activities. Our results showed that all the compounds lacked cytotoxicity against HepG2 cells, whereas 16a and 16b exhibited excellent anticancer activity with IC50 values below 191.57 μM on MCF-7 cell line and also, bis-β-lactams 16a–g showed excellent antitumor activity against the TC-1 cell line. Antioxidant experiments of 16a–d by the diphenylpicrylhydrazyl (DPPH) assay showed IC50 values ranging from 7 to 32.3 μg/ml. Interaction of 16a, 16b, 16d–g with calf-thymus DNA (CT-DNA) was also supported by absorption titration studies. The compounds exhibit good binding propensity to CT-DNA and the DNA binding affinity (Kb) of the compounds varies as 16a; 16b; 16e; 16g > 16d; 16f. Interaction of 16d with CT-DNA was also investigated by fluorescence spectroscopy. The results support an intercalative interaction of 16d and 16f and non-intercalation mechanism for 16a, 16b, 16e, and 16g.
- Borazjani, Nassim,Behzadi, Maryam,Dadkhah Aseman, Marzieh,Jarrahpour, Aliasghar,Rad, Javad Ameri,Kianpour, Sedigheh,Iraji, Aida,Nabavizadeh, S. Masoud,Ghanbari, Mohammad Mehdi,Batta, Gyula,Turos, Edward
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p. 1355 - 1375
(2020/05/14)
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- A 3, 9 - perylene dicarboxylic acid preparation method
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The invention discloses a 3, 9 - perylene dicarboxylic acid of preparation method, specific step is ice-acetic acid in a solvent, in the dihydro e is obtained under the action of the sodium dichromate of 1, 8 - naphthalenedicarboxylic anhydride; 1, 8 - naphthalenedicarboxylic anhydride in saturated ammonia under the action of the acylation to obtain the 1, 8 - naphthalene asia amide; 1, 8 - naphthalene asia amide in potassium hydroxide and anhydrous sodium acetate manufacturing of the alkaline environment in the alkaline environment in C - C under high-temperature conditions obtained by coupling the 3, 4, 9, 10 - perylenetetracarboxylic acid diimide; 3, 4, 9, 10 - perylenetetracarboxylic acid diimide in under the action of the strong acid is converted into the 3, 4, 9, 10 - [...]; 3, 4, 9, 10 - [...] in microwave reactor in alkaline hydrolysis by the decarboxylation of 3, 9 - perylene dicarboxylic acid. The invention synthetic process more economic, environmental protection, high-efficient and simple.
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- Preparation method and application of novel perylene acid medicinal molecule with antineoplastic activity
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The invention discloses a preparation method and application of a novel perylene acid medicinal molecule with antineoplastic activity, and belongs to the technical field of pharmaceutical synthesis. The novel perylene acid medicinal molecule with antineoplastic activity is characterized by having the structural formula as shown in the description. The invention also provides a preparation method of the novel perylene medicinal molecule with the antineoplastic activity. The prepared perylene medicinal molecule has higher inhibiting activity for human cervical carcinoma Hela cells, human breastcancer MDA-MB-231 cells and human liver cancer HepG2 cells, and has the potential of becoming an antineoplastic medicament.
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- Preparation method and application of novel perylene drug molecule with biological activity
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The invention discloses a preparation method and application of a novel perylene drug molecule with the biological activity, and belongs to the technical field of medicine synthesis. According to thekey points of the technical scheme of the preparation method and application of the novel perylene drug molecule, the structural formula of the perylene drug molecule with the biological activity is as shown in the specification, wherein R is O or S. The invention further relates to the preparation method for the novel perylene drug molecule with the biological activity. The perylene drug moleculeprepared through the preparation method has good inhibitory activity on human cervical cancer hHela cells, human breast cancer MDA-MB-231 cells and human liver cancer HepG2 cells, is relatively low in toxicity on human normal cells and has the potential of becoming an anti-tumor drug.
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- Synthesis and Biological Evaluation of Organometallic Complexes Bearing Bis-1,8-naphthalimide Ligands
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Organometallic N-heterocyclic carbene (NHC) complexes with intercalating bis-naphthalimide ligands were prepared and evaluated biologically. Cytotoxic effects against tumor cells or bacteria were strongly ligand dependent with minor influence of the metal (Ag, Ru, Rh, Au) centers. Complex 8b with a rhodium(I) NHC moiety was studied in more detail for its DNA interacting properties in comparison to the metal free ligand. These studies showed a good DNA binding pattern with some preference for the telomeric quadruplex structure hTelo. Complex 8b was also shown to trigger additional coordinative binding to the DNA and therefore represents an useful tool compound with a mixed intercalative/coordinative DNA binding mode.
- Streciwilk, Wojciech,Terenzi, Alessio,Lo Nardo, Federico,Prochnow, Pascal,Bandow, Julia Elisabeth,Keppler, Bernhard K.,Ott, Ingo
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p. 3104 - 3112
(2018/07/29)
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- Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives
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A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.
- Szalay, Roland,Harmat, Veronika,E?ri, János,Pongor, Gábor
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p. 2186 - 2192
(2017/05/16)
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- Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions
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Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.
- Marvi, Omid
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p. 3501 - 3504
(2017/08/14)
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- Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions
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Some aromatic 1,2-dicarbonyl compounds, i.e. 9,10-phenanthrenequinone, acenaphthenequinone and benzil, and their corresponding N-phenyl monoimines, have been reduced, using dry acetonitrile as the solvent, in the presence of sodium cyanide as a reducing agent. Comparative potentiostatic preparative-scale electrolysis is described.
- Batanero, Belen,Hamrouni, Kaouthar,Barba, Fructuoso,Barba, Isidoro,Boujlel, Khaled,Benkhoud, Mohamed Lamine
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p. 1284 - 1288
(2015/12/12)
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- Synthesis and photophysical properties of 1, 4-disubstituted naphthyloxymethyl-N-alkyl naphthimido-1,2,3-triazole
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Regioselective synthesis of a series of 1,4-disubstituted of naphthoxymethyl-N-alkyl naphthalimide-1,2,3-triazoles employing click reaction is presented. Highly selective and efficient copper(I)-catalysed 1,3-dipolar cyclo addition between 1-naphthylpropargylic ether and azido alkyl naphthalimides yielded the title compounds in 74% to 94%. The structure of all the new 1,2,3-triazoles was characterized by 1HNMR, 13C NMR, IR and Mass. The electronic absorption and emission studies revealed that the light absorbing and emitting chromophore is the naphthoxy moiety. There is no extensive delocalization of aromatic π-electrons in the active chromophore which exhibited lower quantum yields and lower Stokes shifts.
- Ramchander,Rameshwar,Reddy, T Sheshashena,Raju, Gajula,Reddy, A Ram
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p. 1063 - 1074
(2014/11/07)
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- Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers
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A facile and efficient microwave-assisted reaction of 1,8-naphthalic anhydride derivatives with primary amines, leading to the synthesis of 1,8-naphthalimides, has been developed. Subsequently, the free radical scavenging properties of the 1,8-naphthalimide derivatives were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH). The results showed that the scavenging activities of compounds 2a, NBNA, 3b, and 3c were more efficient than that of the common synthetic antioxidant 2,6-diterbutyl- 4-methylphenol (BHT), with IC50 values of 61.9, 54.0, 42.2, and 43.1 μM, respectively. The imide groups introduced at position 4 as well as the nitro functionality at position 3 of the naphthalene moiety were the major contributors to the free radical scavenging activities. Springer Science+Business Media, LLC 2010.
- Zhang, Ye,Feng, Shaobo,Wu, Qiang,Wang, Kai,Yi, Xianghui,Wang, Hengshan,Pan, Yingming
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experimental part
p. 752 - 759
(2012/05/20)
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- Formamide, a novel challenging reagent for the direct synthesis of non-N-substituted cyclic imides
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Aliphatic and aromatic cyclic imides have been prepared in high to moderate yields from cyclic carboxylic anhydrides or corresponding dicarboxylic acids, using formamide as reagent at 170-180°C for 5-6 hours. In the case of aromatic products with lower solubility in formamide, we used N-methyl-2-pyrrolidinone (NMP) as supplementary solvent, which facilitates the reaction.
- Chiriac, Constantin I.,Nechifor, Marioara,Tanasǎ, Fulga
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p. 883 - 886
(2008/09/20)
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- Rapid and convenient microwave-assisted synthesis of aromatic imides and N-hydroxymethylimides
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Extremely simple high-yielding and rapid microwave-assisted synthesis of wide array of aromatic mono and diimides and mono- and bis-N-hydroxymethylimides is reported.
- Kacprzak, Karol
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p. 1499 - 1507
(2007/10/03)
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- Process for the manufacture of 1,8-naphthalimide
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A process for preparing 1,8-naphthalimide by reacting 1,8-naphthalic anhydride with ammonia in an aqueous solution under atmospheric pressure at 60 to 100° C.
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Page column 2-4
(2008/06/13)
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- Design and synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrids as anti-tumour agents
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The facile synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrid analogues is described. The compounds are prepared with varying degrees of linker length in order to probe the structural requirements for optimal in vitro anti-tumour activity. Some of these new hybrid compounds showed higher cytotoxic activity than the existing natural and synthetic pyrrolo[2,1-c][1,4]benzodiazepines.
- Kamal, Ahmed,Reddy,Reddy, G.Suresh Kumar,Ramesh
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p. 1933 - 1935
(2007/10/03)
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- Imidation of cyclic carboxylic anhydrides under microwave irradiation
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Efficient and facile conversion of cyclic carboxylic anhydrides to corresponding imides with formamide under microwave irradiation is described.
- Peng,Song,Qian
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p. 1927 - 1931
(2007/10/03)
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- The UV-Visible Absorption and Fluorescence of some Substituted 1,8-Naphthalimides and Naphthalic Anhydrides
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A number of substituted 1,8-naphthalimides and naphthalic anhydrides have been prepared and their absorption and fluorescence properties in absolute ethanol have been determined.In the absence of an alkylamino substituent in the naphthalene ring, the compounds are colourless and weakly fluorescent.In the presence of such a substituent they become yellow and frequently fluoresce strongly with quantum yields of the order of 0.8.
- Alexiou, Michael S.,Tychopoulos, Vasiliki,Ghorbanian, Shohreh,Tyman, John H. P.,Brown, Robert G.,Brittain, Patrick I.
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p. 837 - 842
(2007/10/02)
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- Process for the preparation of naphthalene-1,8-dicarboximides
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Process for the preparation of naphthalene-1,8-dicarboximide which is optionally substituted in the naphthalene ring, characterized in that naphthalene-1,8-dicarboxylic anhydride which is optionally substituted in the naphthalene ring is reacted with an ammonium salt in an aqueous medium at a pH near to the neutral point, the reaction mixture is then acidified to a pH of 1 to 4 and the pH is subsequently adjusted to a value near to the neutral point.
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- REACTION OF AROMATIC DI- AND TETRACARBOXYLIC ANHYDRIDES WITH AMIDES
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In the reaction of aromatic di- and tetracarboxylic anhydrides containing carboxyl groups at the ortho and peri position with amides the corresponding mono- and diimides were obtained.The reaction of phthalic anhydride with formamide, leading to phthalimide, takes place with the intermediate formation of N-formylphthalamic acid.
- Ganin, E. V.,Makarov, V. F.,Nikitin, V. I.
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p. 981 - 983
(2007/10/02)
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- Photochemical Electron-transfer Reactions of Biphenyl-2,2'-dicarboximide and Naphthalene-1,8-dicarboximide with Olefin. Dependence of the Reaction Course on the Structure of the Aromatic Imide
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Photoreactions of N-methylbiphenyl-2,2'-dicarboximide and N-ethylnaphthalene-1,8-dicarboximide (2) with 1,1-diphenylethylene (3) in methanol gave methanol-incorporated 1:1:1-adduct (7) and 2,2-diphenylethyl methyl ether (6), an anti-Markovnikov adduct of methanol to 3.The ratio of the two types of products largely depends on the structure of the aromatic imides.Probably the spin densities of the radical anions of the aromatic imides seem to play an important role to determine the reaction courses after the photochemical electron-transfer process.Similar results were obtained in the photoreaction of N-(2-phenylallyl)aromatic imides; elimination induced by methanol-incorporation vs. anti-Markovnikov addition of methanol. Photoreactions of N-(trans-3-phenylallyl) aromatic imides in methanol gave methanol-incorporated O-cyclized products (20 and 27) and C-cyclized products (21 and 28).A tentative mechanism for the O-cyclization is proposed; i.e., intramolecular electron transfer followed by anti-Markovnikov addition of methanol to the radical cation of the double bond moiety, nucleophilic attack of the aromatic imide radical anion moiety, secondary electron-transfer, and then polar addition of methanol.
- Kubo, Yasuo,Araki, Takeo,Maruyama, Kazuhiro
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p. 2863 - 2869
(2007/10/02)
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- PHOTO-INDUCED HIGHLY SELECTIVE OLEFIN-MIGRATION OF N-(2- OR 3-PHENYLALLYL) AROMATIC IMIDES
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A highly selective migration of double bond was observed on irradiation of N-(2- or 3-phenylallyl) aromatic imides in acetonitrile to afford N-(2- or 3-phenyl-1-propenyl) aromatic imides.The reaction seems to proceed via photochemical intramolecular one electron transfer from the double bond to the imide moiety.
- Kubo, Yasuo,Araki, Takeo,Maruyama, Kazuhiro
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p. 1909 - 1912
(2007/10/02)
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