Thermal and Photochemical Reactions of η5-Cyclopentadienyl(naphthoyl)(dicarbonyl)iron Complexes with Alkynes: Formation of Benzindenones and Dihydropentalenones

DOI: 10.1039/P19900002799

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2799 - 2805 (1990)

Update date:2022-08-02

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Authors:

Butler, Ian R.

Charland, Jean-Pierre

Elliot, Joanne L.

Houde, Jean

Lindsell, W. Edward

et al. et al.

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Article abstract of DOI:10.1039/P19900002799

η⁵-Cyclopentadienyl(1- and 2-naphthoyl)(dicarbonyl)iron complexes (6a) and (6b) have been synthesised from the appropriate acid chlorides and sodium η⁵-cyclopentadienyl(dicarbonyl)iron(1-).UV irradiation of (6a) and (6b) separately with diphenylacetylene in benzene gives 1,2-diphenyl-3H-benzinden-3-one (8), and 2,3-diphenyl-1H-benzinden-1-one (7) respectively, together with smaller quantities of bis(η⁵-cyclopentadienyl)(tetracarbonyl)di-iron.The benzindenones (7) and (8) are also formed in low yield from diphenylacetylene and η⁵-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 η⁵-cyclopentadienyl(1-naphthoyl)(dicarbonyl)iron with 1-phenylpropyne.The molecular structures of (7) and (9a) were elucidated by X-ray crystallography.

Full text of DOI:10.1039/P19900002799

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