Coupling reactions of ferrocenylacetylene with mononuclear metal carbonyls Fe(CO)5 and M(CO)6 (M = Mo, W): synthesis and characterization of [Fe(CO)25-2,5-Fc2C5H2CO}C(Fc)CH], [Fe(CO)222-2,5-Fc2C4H2Fe(CO)3}-μ-CO], [Fe(CO)322-2,5-Fc2C4H2CO}], 1,2,4-Triferrocenylbenzene, 2,5-diferrocenylthiophene, and 2,5-diferrocenylselenophene

Mathur, Pradeep ; Singh, Amrendra K. ; Singh, Vinay K. ; Singh, Priti ; Rahul, ; Mobin, Shaikh M. ; Thone, Carsten (2005) Coupling reactions of ferrocenylacetylene with mononuclear metal carbonyls Fe(CO)5 and M(CO)6 (M = Mo, W): synthesis and characterization of [Fe(CO)25-2,5-Fc2C5H2CO}C(Fc)CH], [Fe(CO)222-2,5-Fc2C4H2Fe(CO)3}-μ-CO], [Fe(CO)322-2,5-Fc2C4H2CO}], 1,2,4-Triferrocenylbenzene, 2,5-diferrocenylthiophene, and 2,5-diferrocenylselenophene Organometallics, 24 (20). pp. 4793-4798. ISSN 0276-7333

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Official URL: http://pubs.acs.org/doi/abs/10.1021/om0504755

Related URL: http://dx.doi.org/10.1021/om0504755

Abstract

Thermolysis of a benzene solution containing Fe(CO)5 and ferrocenylacetylene yielded three new compounds: [Fe(CO)25-2,5-Fc2C5H2CO}C(Fc)=CH] (1), [Fe(CO)222-2,5-Fc2C4H2Fe(CO) 3 }-μ-CO] (2), and [Fe(CO)322-2,5-Fc2C4H2CO}] (3). When a benzene solution containing ferrocenylacetylene and M(CO)6 (M = Mo, W) was refluxed, 1,2,4-triferrocenylbenzene (4) was formed. In contrast to the reaction of ferrocenylacetylene with Fe(CO)5, which leads to cyclization with insertion of a CO molecule, in the reaction with M(CO)6 no insertion of CO takes place during cyclization. However, if the reactions with M(CO)6 are carried out in the presence of S8-powder or Se-powder, insertion of these chalcogen atoms during cyclization does take place and 2,5-diferrocenylthiophene (5) and 2,5-diferrocenylselenophene (6) are formed respectively, along with 4. All new compounds were characterized by IR and 1H and 13C NMR spectroscopy. Structures of 1-5 were established by single-crystal X-ray crystallography.

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