Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement

doi:10.1007/s40242-015-4356-3

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (2): 224-227.doi: 10.1007/s40242-015-4356-3

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Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement

ZHANG Ran, XU Lihua, CHEN Hui, QIN Zhihong, ZHAO Yu, Ni Zhonghai

School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221116, P. R. China

Received:2014-09-23 Revised:2014-10-20 Online:2015-04-01 Published:2014-11-10
Contact: Ni Zhonghai E-mail:nizhonghai@cumt.edu.cn
Supported by:
Supported by the National Basic Research Program of China(No.2012CB214900), the National Natural Science Foundation of China(No. 21176246) and the Jiangsu QingLan Project, China.

Abstract

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.

Key words: Newman-Kwart rearrangement, 1-Thiohydroxypyrene, Crystal structure

ZHANG Ran, XU Lihua, CHEN Hui, QIN Zhihong, ZHAO Yu, Ni Zhonghai. Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement[J]. Chemical Research in Chinese Universities, 2015, 31(2): 224-227.

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Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement

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