Zethrene

Synthesis

The compound was originally synthesized by Erich Clar in 1955 from acenaphthene in one method and from chrysene in another. Mitchell and Sondheimer prepared the compound from a benzannulated [10]annulene.

A sulfur extrusion method was reported by Kemp, Storie, and Tulloch. Wu et al. reported the synthesis of the compound in a coupling reaction / dimerization with in-situ desilylation.

A Heck variation was reported in 2013.

Derivatives are also known.

Structure

X-ray crystallography indicates that zethrene is a planar molecule. The bond lengths in the central part of the molecule are consistent with distinct single and double bonds rather than aromatic components.

References

References

1. (1955). "Aromatische Kohlenwasserstoffe, LXX. Mitteil.1): Zethren (1.12; 6.7-Dibenztetracen)". [[Chemische Berichte]].
2. (1968). "A dinaphth[10]annulene". [[Journal of the American Chemical Society]].
3. (1970). "The attempted synthesis of a dinaphth-1,6-bisdehydro[10]annulene". [[Tetrahedron (journal).
4. (1980). "Synthesis of potentially basic hydrocarbons by sulphur extrusion and/or bis-Wittig reactions. Two syntheses of benz[5,6]indeno[2,1-a]phenalene and a new synthesis of {{chem name". Journal of the Chemical Society, Perkin Transactions 1.
5. (2010). "Synthesis, Structure, and Photophysical Properties of {{chem name". [[Angewandte Chemie International Edition]].
6. (2013). "Revisiting zethrene: Synthesis, reactivity and semiconductor properties". Chemical Science.
7. (2009). "Tetradehydrodinaphtho[10]annulene: A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives". [[Organic Letters]].
8. (2010). "Soluble and Stable Zethrenebis(dicarboximide) and Its Quinone". [[Organic Letters]].