Reactive iron carbonyl reagents via reaction of metal alkoxides with Fe(CO)5 or Fe2(CO)9: synthesis of cyclobutenediones via double carbonylation of alkynes |
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Authors: | Beesu Mallesh Periasamy Mariappan |
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Affiliation: | School of Chemistry, University of Hyderabad, Hyderabad 500046, India. |
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Abstract: | Alkoxy bases such as t-BuOK react with Fe(CO)(5) to give reactive iron carbonyl intermediates that in turn react with alkynes at 70 °C in THF to give 1,2-cyclobutenediones in 70-93% yields after CuCl(2)·2H(2)O oxidation. A novel 1,2-diacyloxyferrole derivative was isolated in the reaction of diphenylacetylene with Fe(CO)(5)/t-BuOK in the presence of acetyl chloride in contrast to the formation of a 1,4-diacyloxyferrole complex formed in the reaction using Fe(CO)(5)/Me(3)NO. The Fe(2)(CO)(9)/t-BuOK reagent system also converts the alkynes to corresponding cyclobutenediones in 63-90% yields under similar reaction conditions. |
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