Abstract
AbstractDithiole and cyclopentadiene rings have been introduced into functionalised cyclopropa[b]naphthalenes to provide highly coloured, conjugated and cross‐conjugated π‐extended derivatives that have varying stability. Cyclopentadienylidene‐containing cyclopropanaphthalene 18 and its dithiolylidene analogue 25 are prepared from bromophenylcyclopropanaphthalene 12, and the 1,1‐biscyclopentadienylidene 20 from dibromide 13. Use of dithiole‐containing ketones with 1,1‐bis(trimethylsilyl)cyclopropa[b]naphthalene 10 gives the π‐extended cycloproparenes 27 and 29 in Peterson olefinations that are more efficient than Wittig−Horner reactions of cyclopropanthraquinone 31 with dithiolate 24 to give the cross‐conjugated cycloproparenes 34 and 35. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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