Synthesis of Polycyclic Aromatics With Unusual Architectures

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. A new synthetic approach to 2,2 -disubstituted 1,1 - binaphthyls and related compounds was also successfully developed 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.

Autorentext

Yu-Hsuan(Lily) Wang, Ph.D.: Born and raised in Taiwan, R.O.C., Lily came to the United States in 2003 to study organic chemistry at West Virginia University. In August of 2008, she received her Ph.D. degree. Currently, she is an associate investigator in TaiGen Biotechnology CO., Ltd., Taipei.

Klappentext

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. A new synthetic approach to 2,2'-disubstituted 1,1'- binaphthyls and related compounds was also successfully developed 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.