"Synthesis of novel polycyclic aromatics and heteroaromatics via cascad" by Hua Yang

Semester

Spring

Date of Graduation

2006

Document Type

Dissertation

Degree Type

PhD

College

Chambers College of Business and Economics

Department

Economics

Committee Chair

Kung K Wang

Abstract

Studies on the thermal cyclization of enyne-isocyanates led to a new synthetic pathway to synthesize heterocycles. It was found that the enyne-isocyanates underwent predominantly C2--C7 cyclization at high temperature and the cycloaromatization was facilitated by the addition of silyl chloride.;The C2--C6 Schmittel cyclization of benzannulated enyne-allenes can provide efficient synthetic pathway for the polycyclic aromatics. As a result, new synthetic pathways to synthesize the 1,2-bis[5-(11 H-benzo[b]fluorenyl)]benzenes and related compounds were developed by employing the Schmittel cyclization reaction. The nonbonded steric interaction led to the formation of syn-isomers as major products, which hold potential to complex with transition metals to catalyze the olefin polymerization. Furthermore, another synthetic pathway to 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds was also successfully developed by using BINOL as starting material. Several enantiomerically pure syn atropisomers, which hold potential as hetero-bi-dentate ligands for asymmetric catalysis, were prepared.;Moreover, a simple and efficient pathway involving the Schmittel cyclization reaction was developed to synthesize novel polycyclic aromatics having a 54-carbon framework represented on the surface of C60. They could serve as potential precursors for a novel buckybasket.*.;*This dissertation is a compound document (contains both a paper copy and a CD as part of the dissertation). The CD requires the following system requirements: Adobe Acrobat.

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