Cycloocta [def] fluorene: A Planar Cyclooctatetraene Derivative. 1 Paratropicity of Hydrocarbon and Anion

Itamar Willner, Mordecai Rabinovitz*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

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 languageEnglish
Pages (from-to)1628-1633
Number of pages6
JournalJournal of Organic Chemistry
Volume45
Issue number9
DOIs
StatePublished - Apr 1980

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