Convenient Synthesis of 1-Thiohydroxypyrene by Newman-Kwart Rearrangement

被引：5

作者：

Zhang Ran ^{[1
]}

Xu Lihua ^{[1
]}

Chen Hui ^{[1
]}

Qin Zhihong ^{[1
]}

Zhao Yu ^{[1
]}

Ni Zhonghai ^{[1
]}

机构：

[1] China Univ Min & Technol, Sch Chem Engn & Technol, Xuzhou 221116, Peoples R China

来源：

CHEMICAL RESEARCH IN CHINESE UNIVERSITIES | 2015年 / 31卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Newman-Kwart rearrangement; 1-Thiohydroxypyrene; Crystal structure; PYRENE; DERIVATIVES; MERCAPTO;

D O I：

10.1007/s40242-015-4356-3

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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.

引用

页码：224 / 227

页数：4

共 21 条

[1] New sulfur-containing host materials for blue phosphorescent organic light-emitting diodes [J].

Bin, Jong-Kwan ;

Yang, JoongHwan ;

Hong, Jong-In .

JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (40) :21720-21726

[2] 1,2,4-triazolo mercapto and aminonitriles as potent antifungal agents [J].

Collin, X ;

Sauleau, A ;

Coulon, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) :2601-2605

[3] Synthesis of structurally modified atropisomeric biaryl dithiols. Observations on the Newman-Kwart rearrangement [J].

Cossu, S ;

DeLucchi, O ;

Fabbri, D ;

Valle, G ;

Painter, GF ;

Smith, RAJ .

TETRAHEDRON, 1997, 53 (17) :6073-6084

[4]

Coyle J. D., 1975, CHEM SOC REV, P523

[5]

Cristiano Z., 2007, TOP CURR CHEM, P131

[6] Pyrene-Based Materials for Organic Electronics [J].

Figueira-Duarte, Teresa M. ;

Muellen, Klaus .

CHEMICAL REVIEWS, 2011, 111 (11) :7260-7314

[7]

Harvey J.N., 2009, Angewandte Chemie, V121, P7748

[8] Highly fluorescent crystalline and liquid crystalline columnar phases of pyrene-based structures [J].

Hayer, A ;

de Halleux, V ;

Köhler, A ;

El-Garoughy, A ;

Meijer, EW ;

Barberá, J ;

Tant, J ;

Levin, J ;

Lehmann, M ;

Gierschner, J ;

Cornil, J ;

Geerts, YH .

JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (15) :7653-7659

[9] Syntheses, crystal structures, and spectral properties of a series of 3,8-bisphenyl-1,10-phenanthroline derivatives:: Precursors of 3,8-bis(4-mercaptophenyl)-1, 10-phenanthroline and its ruthenium(II) complex for preparing nanocomposite junctions with gold nanoparticles between 1 μm gap gold electrodes [J].

Huang, Wei ;

Masuda, Gou ;

Maeda, Seisuke ;

Tanakat, Hirofurni ;

Hino, Takarni ;

Ogawa, Takuji .

INORGANIC CHEMISTRY, 2008, 47 (02) :468-480

[10] Thiophenol Analogs of Tocopherols and Tocotrienols [J].

Hyatt, John A. ;

Dycus, Megan ;

Chau Nguyen ;

Little, James L. .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2012, 44 (03) :256-261

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