Concise synthesis of halogenated chrysenes ([4]phenacenes) that favor pi-stack packing in single crystals.
A concise synthesis of halogenated chrysene derivatives from 2,2,2-trifluoroethyl tosylate and halostyrene was established. Friedel-Crafts type cyclization of a 1,1-difluoro-1-alkene bearing halogenated phenyl moieties involved skeletal rearrangement and dehydrogenation to afford the title compound in good to moderate yield. X-ray analysis revealed that the halogen substituents induce pi-stack packing of the molecules in the crystals.
Isobe
Hiroyuki
H
Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan. isobe@m.tains.tohoku.ac.jp
Hitosugi
Shunpei
S
Matsuno
Taisuke
T
Iwamoto
Takeaki
T
Ichikawa
Junji
J