Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement |
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Authors: | ZHANG Ran XU Lihua CHEN Hui QIN Zhihong ZHAO Yu Ni Zhonghai |
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Institution: | School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221116, P. R. China |
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Abstract: | 1-Thiohydroxypyrene(1) and its two intermediates, 1-pyrenyl-O-thiocarbamate(2) and 1-pyrenyl-S-thio- carbamate(3), were synthesized using 1-hydroxypyrene as the starting material. The key synthetic step is Newman-Kwart rearrangement. The results indicate that the Newman-Kwart rearrangement is more effective in suitable solvent than conventional method based on pure organic compound. The structures of compounds 1―3 were characterized by FTIR, NMR, GC-MS and elementary analysis. The crystal structures of two new compounds(2 and 3) were determined by single crystal X-ray diffraction analysis. The whole synthetic process is simple, mild and with high yield. |
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Keywords: | Newman-Kwart rearrangement 1-Thiohydroxypyrene Crystal structure |
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