[CH2:1]([N:4]1[C:13](=[O:14])[CH:8]2[CH2:9][CH:10]=[CH:11][CH2:12][CH:7]2[C:5]1=[O:6])[CH:2]=[CH2:3].NCP(=O)(O)[OH:18].O.OO>S([O-])(O)(=O)=O.C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[O:18]1[CH:11]2[CH:10]1[CH2:9][CH:8]1[C:13](=[O:14])[N:4]([CH2:1][CH:2]=[CH2:3])[C:5](=[O:6])[CH:7]1[CH2:12]2In a 50 mL three-necked flask equipped with stirrer, dropping funnel and Dimroth condenser tube there were charged 5.15 g of N-allyl-4-cyclohexene-1,2-dicarboximide, 0.23 g of methyltrioctylammonium hydrogensulfate, 0.22 g of sodium tungstate dihydrate and 0.03 g of aminomethylphosphonic acid. The mixture was heated using an oil bath kept at 90° C., and after adding 4 ml of 30% hydrogen peroxide water dropwise over a period of 30 minutes through a dropping funnel, the mixture was aged for 4 hours. It was then cooled in an ice bath, and after removing the excess hydrogen peroxide with 15 mL of saturated aqueous sodium thiosulfate, extraction was performed 5 times with 10 mL of ethyl acetate. The obtained ethyl acetate solution was dried overnight over anhydrous sodium sulfate, a rotary evaporator was used to remove the ethyl acetate solvent to obtain 3.21 g of a crude product of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide, and then purification was performed by chromatography with a column packed with 25% hydrated silica gel. Structural isomers of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide exist due to the epoxy group, and of these there were obtained 0.72 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 and 0.56 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 2. An AL-400 nuclear magnetic resonance apparatus by JEOL Corp. was used to measure the 1H-NMR and 13C-NMR spectra of the 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 in a heavy chloroform solvent, thus allowing confirmation of the structure. The 1H-NMR and 13C-NMR spectra of the 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 are shown in FIGS. 1 and 2, respectively, and the 1H-NMR integral values of the 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 are shown in Table 1 below.
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