American Chemical Society
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Improved Synthesis of Pentabenzylcyclopentadiene and Study of the Reaction between Pentabenzylcyclopentadiene and Iron Pentacarbonyl

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journal contribution
posted on 1996-05-28, 00:00 authored by Woei-Min Tsai, Marvin D. Rausch, Robin D. Rogers
An improved synthetic route to pentabenzylcyclopentadiene, C5Bz5H (1), has been developed, utilizing a larger amount of dicyclopentadiene, sodium, and excess benzyl alcohol as both reactant and solvent. Subsequent extraction and crystallization using hexane produced 1 in 62% yield. A reaction between 1 and iron pentacarbonyl in refluxing toluene led to the formation of [(η5-C5Bz5)Fe(CO)2]2 (2) and (η4-C5Bz5H)Fe(CO)3 (3). Unlike the parent compound (η4-C5H6)Fe(CO)3, 3 exhibited exceptional air and thermal stability. A single-crystal X-ray diffraction study of 3 has been undertaken and confirms the proposed structure.