Reactive iron carbonyl reagents via reaction of metal alkoxides with Fe(CO) 5 or Fe 2(CO) 9: Synthesis of cyclobutenediones via double carbonylation of alkynes

Mallesh Beesu, Mariappan Periasamy

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

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 2O 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 3NO. The Fe 2(CO) 9/t-BuOK reagent system also converts the alkynes to corresponding cyclobutenediones in 63-90% yields under similar reaction conditions.

Original languageEnglish (US)
Pages (from-to)543-549
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number2
DOIs
StatePublished - Jan 21 2011

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