Issue 14, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Studies in the cycloproparene series: chemistry of 1H-cyclopropa[b]naphthalene-3,6-dione and its transformation into 1H-cyclopropa[b]anthracene-3,8-dione1

Brian Halton,*a   Carissa S. Jones,a   Andrew J. Kay,†a   Davor Margeticb  and  Sanja Sretenovica  

* Corresponding authors

a School of Chemical & Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand

b Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, Australia

Abstract

1H-Cyclopropa[b]naphthalene-3,6-dione 3 adds bromine stoichiometrically across the enedione C[double bond, length half m-dash]C bond to give dibromodihydrocyclopropanaphthalenedione 10 while with an excess of the reagent (bromomethyl)tribromonaphthoquinone 12 is formed. Typical quinone character is exhibited by 3 in Diels–Alder cycloadditions and it gives the endo-methanocyclopropanthraquinone 14 with cyclopentadiene. With buta-1,3-diene the analogous tetrahydrocyclopropanthraquinone 15 is formed from a temperature dependent reaction. Above 45 °C opening of the three-membered ring of 4 also occurs and the cyclopentanthracenedione 16 is obtained from [π2 + π4] and [σ2 + π2] additions; it is the sole product at 100 °C. Enolisation of the tetrahydroanthraquinone 15 provides diphenolate 18 and this can be diverted to diether 19 or readily oxidized to the dihydroanthraquinone 20. In turn, 20 is dehydrogenated to the fully aromatic cyclopropa[b]anthracene-3,8-dione 4, the first anthraquinone of the cycloproparene series.

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Article information

DOI
https://doi.org/10.1039/B002683M
Article type
Paper
Submitted
04 Apr 2000
Accepted
02 Jun 2000
First published
03 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2205-2210

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Studies in the cycloproparene series: chemistry of 1H-cyclopropa[b]naphthalene-3,6-dione and its transformation into 1H-cyclopropa[b]anthracene-3,8-dione1

B. Halton, C. S. Jones, A. J. Kay, D. Margetic and S. Sretenovic, J. Chem. Soc., Perkin Trans. 1, 2000, 2205 DOI: 10.1039/B002683M

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