Sterically hindered tricarbonyl(cyclohexadiene)iron complexes: preparation, isomer formation and isomerization reactions

Add time:08/09/2019    Source:sciencedirect.com

The reaction of Fe(CO)5 with 1-alkoxy-4-alkyl-cyclohexa-1,3-dienes, in which the alkyl substituent is a sterically demanding group such as isopropyl or tert-butyl, has been studied. An unprecedented rearrangement of the 1,3-diene was found to take place during the reaction to give a mixture of Fe(CO)3-complex isomers. Tricarbonyl[(1,4-η)-2-isopropyl-5-tert-butyl-cyclohexa-1,3-diene]iron was the predominant product after p-toluenesulfonic acid-catalyzed isomerization of a mixture of isomers. This is in contrast to tricarbonyl[(1,4-η)-1-isopropoxy-4-ethyl- or methyl-cyclohexa-1,3-diene]iron which is a more stable form. Thus, the stability of the isomer of the Fe(CO)3 complexes is also controlled by the bulkiness of the C-4 alkyl substituents.

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