Thermal and photochemical reactions of η5- cyclopentadienyl(naphthoyl)-(dicarbonyl)iron complexes with alkynes: Formation of benzindenones and dihydropentalenones

Ian R. Butler, Jean Pierre Charland, Joanne L. Elliot, Jean Houde, W. Edward Lindsell, Kevin J. McCullough, Peter N. Preston, Alan B. Rettie

Research output: Contribution to journalArticle

Abstract

?5-Cyclopentadienyl(1- and 2-naphthoyl)(dicarbonyl)iron complexes (6a) and (6b) have been synthesised from the appropriate acid chlorides and sodium ?5-cyclopentadienyl(dicarbonyl)iron-(1-). UV irradiation of (6a) and (6b) separately with diphenylacetylene in benzene gives 1,2-diphenyl-3H-benz[e]inden-3-one (8), and 2,3-diphenyl-1H-benz[e]inden-1-one (7) respectively, together with smaller quantities of bis(?5- cyclopentadienyl)(tetracarbonyl)di-iron. The benz[e]indenones (7) and (8) are also formed in low yield from diphenylacetylene and ?5- cyclopentadienyl(1- and 2-naphthoyl)(dicarbonyl)iron complexes respectively, in hot decalin. A second product from the thermal reaction is c-4,c-6a-dihydro-4- (1- or 2-naphthyl)-2,3-diphenylpentalen-1(r-3aH)-one (9a) or (9b), respectively, incorporating a cyclopentadienyl group. A compound of the last type (9c) is also formed in a thermal reaction of ?5-cyclopentadienyl(1- naphthoyl)(dicarbonyl)iron with 1-phenylpropyne. The molecular structures of (7) and (9a) were elucidated by X-ray crystallography.

Original languageEnglish
Pages (from-to)2799-2805
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number10
Publication statusPublished - 1990

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    Butler, I. R., Charland, J. P., Elliot, J. L., Houde, J., Lindsell, W. E., McCullough, K. J., Preston, P. N., & Rettie, A. B. (1990). Thermal and photochemical reactions of η5- cyclopentadienyl(naphthoyl)-(dicarbonyl)iron complexes with alkynes: Formation of benzindenones and dihydropentalenones. Journal of the Chemical Society, Perkin Transactions 1, (10), 2799-2805.