Thermal cyclization of 7,10-diethynylfluoranthene
(3) in the gas phase gives corannulene (2), the
smallest
bowl-shaped polycyclic hydrocarbon fragment of C60 with
fullerene-like curvature. Bromocorannulene (10)
and
1,6-dibromocorannulene (9) have also been obtained from
flash pyrolysis of
7,10-bis(2,2-dibromovinyl)fluoranthene
(8). Short, practical syntheses of several corannulene
precursors from acenaphthenequinone are described which
have made corannulene available in gram quantities.
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