Semester
Summer
Date of Graduation
2008
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Kung K Wang
Abstract
The C2-C6 Schmittel cyclization reaction of the benzannulated enyne-allenes provides an efficient synthetic pathway for the construction of a variety of polycyclic aromatics. By starting from truxenone, the cascade cyclization reactions furnished several unusual and congested polycyclic compounds. The in situ generated enyne-allenes are key intermediates in these cyclization reactions.;A new synthetic approach to 2,2'-disubstituted 1,1'-binaphthyls and related compounds was also successfully developed by using the benzannulated enediynes as precursors. These 1,1'-binaphthyls derivatives can serve as potential BINOL type ligands. The assembly of the enediynyl precursors from three separate aromatic fragments allows the possibility of placing a variety of functional groups at various positions of the 1,1'-binaphthyl system.;A 12-step non-pyrolytic synthetic pathway employing the Schmittel cyclization reactions has been developed, leading to a bowl-shaped polycyclic aromatic hydrocarbon (PAH) having a 54-carbon framework of the surface of C60 . Incorporating of sp3-carbons on the 54-carbon framework facilitates the connection of carbon atoms intramolecularly.
Recommended Citation
Wang, Yu-Hsuan, "Synthesis of polycyclic aromatics having unusual molecular architectures via cascade cyclization reactions of enyne -allenes" (2008). Graduate Theses, Dissertations, and Problem Reports. 4430.
https://researchrepository.wvu.edu/etd/4430