*Please refer to dissertation for diagrams. / In addition, a precursor of tetraphenylene-based monodentate ligand ( S,S)-114 was also prepared, and the structures of five compounds, namely 89, 124, 125, 133 and 137 were examined by X-ray crystallographic analysis. These structural determinations were relevant in establishing regiochemistry and absolute stereochemistry.* / In the synthesis of enantiopure (S,R,S)-48 and (R,S,R)-48, two routes were successfully employed. One way was to follow the same pathway for the synthesis of racemic 48 by using enantiopure (S,S)- and (R,R)-1,8,9,16-teramethoxytetraphenylenes [(S,S)-89 and (R,R)- 89] as staring materials. Another way was by direct resolution of racemic 48 via derivatization into its two diastereomeric hexakis-(S)-camphorsulfonates 135 and 136. / In the synthesis of racemic 48, 3-nitrophenol (115) was employed as the starting material which upon a series of standard reactions provided 2,2'-diiodo-1,1'-biphenyl (119). Through sequential lithium-iodine exchange and Cu(II)-mediated oxidative cyclocoupling, 119 was converted to 1,8,9,16-tetramethoxytetraphenylene (89) . The key intermediate 1,8-dihydroxy-9,16-dimethoxytetraphenylene (87) was obtained by partial demethylation of 89. This intermediate was transformed to 1,4,5,8-tetrahydroxy-9,16-dimethoxytetraphenylene (126) by a quinone-hydroquinone strategy. Demethylation of 126 furnished the target compound 48. / This thesis describes the synthesis of 1,4,5,8,9,16-hexahydroxytetraphenylene (48)* in its racemic and enantiopure (S,R,S) and ( R,S,R) forms. Some essential background and previous works in this area are presented in the first chapter. / Wu Anhui. / "August 2006." / Adviser: Henry N. C. Wong. / Source: Dissertation Abstracts International, Volume: 68-03, Section: B, page: 1649. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2006. / Includes bibliographical references (p. 80-85). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese. / School code: 1307.
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_343901 |
| Date | January 2006 |
| Contributors | Wu, Anhui., Chinese University of Hong Kong Graduate School. Division of Chemistry. |
| Source Sets | The Chinese University of Hong Kong |
| Language | English, Chinese |
| Detected Language | English |
| Type | Text, theses |
| Format | electronic resource, microform, microfiche, 1 online resource (ix, 154 p. : ill.) |
| Rights | Use of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/) |
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