Progress towards a new buckyball fragment

ORGN 531

Kirby A. Underwood, underwood.30@wright.edu and William A. Feld, william.feld@wright.edu. Department of Chemistry, Wright State University, 3640 Col Glenn Hwy, Dayton, OH 45435
It has been previously established that a sequence of reactions starting with 3,4-diphenyl-2,5-dicarboethoxycyclopentadienone can be used to synthesize 5,8-dioxo-5,8-dihydroindeno[2,1-c]fluorene I in an overall yield of 78%. This is an improved efficiency over the previously reported values of 1-9%. The diketone I can be reduced afford 5,8-dihydroindeno[2,1-c]fluorene II in 80% yield. Currently, avenues to oxidize II to produce the curved aromatic ring structure dicyclopenta[def,jkl]triphenylene III are being explored. This generation of the triphenylene represents a new approach to the synthesis of fragments of the C60 surface.