TY - JOUR
T1 - Reactive iron carbonyl reagents via reaction of metal alkoxides with Fe(CO) 5 or Fe 2(CO) 9
T2 - Synthesis of cyclobutenediones via double carbonylation of alkynes
AU - Beesu, Mallesh
AU - Periasamy, Mariappan
PY - 2011/1/21
Y1 - 2011/1/21
N2 - 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.
AB - 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.
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U2 - 10.1021/jo102104a
DO - 10.1021/jo102104a
M3 - Article
C2 - 21192644
AN - SCOPUS:78651513602
SN - 0022-3263
VL - 76
SP - 543
EP - 549
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -