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

Itamar Willner; Mordecai Rabinovitz

doi:10.1021/jo01297a018

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

Itamar Willner, Mordecai Rabinovitz^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	1628-1633
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	45
Issue number	9
DOIs	https://doi.org/10.1021/jo01297a018
State	Published - Apr 1980

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

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.",

author = "Itamar Willner and Mordecai Rabinovitz",

year = "1980",

month = apr,

doi = "10.1021/jo01297a018",

language = "אנגלית",

volume = "45",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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AU - Willner, Itamar

AU - Rabinovitz, Mordecai

PY - 1980/4

Y1 - 1980/4

N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

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

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