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Chemistry and Industry of Forest Products ›› 2018, Vol. 38 ›› Issue (6): 110-116.doi: 10.3969/j.issn.0253-2417.2018.06.015

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Synthesis and Characterization of 3'-(3,3-Dimethylbicyclo[2.2.1] hept-2-ylidene)-5'-phenyl-isoxazoline

HUANG Jing1, BAO Han2, ZHANG Xia1, MO Yue1, LUO Jinyue1, LIU Zuguang3   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    2. Jinling High School, Nanjing 210005, China;
    3. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530006, China
  • Received:2018-07-26 Online:2018-12-25 Published:2018-12-27

Abstract: The unreported 3'-(3,3-dimethylbicyclo[2.2.1] hept-2-ylidene)-5'-phenyl-isoxazoline was synthesized by cycloaddition reaction of 2-(3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)acetaldehyde oxime (camphene aldoxime, CAO) and syrene. The structure of the product was identified by FT-IR, GC-MS, 1H NMR and 13C NMR. The effects of the types of solvent, type and dosage of catalyst, amount of oxidant Oxone, dosage of syrene and reaction time on reaction rate and product yield were discussed. The optimum conditions were obtained as follows:potassium chloride as the catalyst, 50% methanol as solvent, n(camphene aldoxime):n(potassium chloride):n(Oxone):n(syrene)=1.0:0.5:1.5:2.0, reaction time 10 h. Under the above conditions, the product yield was 88.07%.

Key words: camphene aldoxime, cycloaddition reaction, isoxazoline compound, structure characterization

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