Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement

doi:10.1007/s40242-015-4356-3

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (2): 224-227.doi: 10.1007/s40242-015-4356-3

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

收稿日期:2014-09-23 修回日期:2014-10-20 出版日期:2015-04-01 发布日期:2014-11-10
通讯作者: Ni Zhonghai E-mail:nizhonghai@cumt.edu.cn
基金资助:
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.

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.

摘要/Abstract

摘要：

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.

关键词: Newman-Kwart rearrangement, 1-Thiohydroxypyrene, Crystal structure

Abstract:

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]. 高等学校化学研究, 2015, 31(2): 224-227.

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

Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement

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