Abstract
The synthesis of cy cloocta [def] fluorene (1) from cyclopenta [def] phenanthrene (5) is described. Hydrocarbon 1 shows paratropic antiaromatic character as deduced from the 1H NMR spectra and its low acidity (pKa = 27). The antiaromatic character of 1 is attributed to the presence of a planar cyclooctatetraene (COT) moiety. The deprotonation and the formation of cycloocta [def] fluorenyl anion (13) are presented. The anion 13 exhibits paratropic character which may originate in peripheral delocalization of 16 π electrons.
Original language | English |
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Pages (from-to) | 1628-1633 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 45 |
Issue number | 9 |
DOIs | |
State | Published - Apr 1980 |