American Chemical Society
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Tetrahydrofurfuryloxide Derivatives of Alkyl Aluminum Species

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posted on 2005-02-14, 00:00 authored by Timothy J. Boyle, Todd M. Alam, Scott D. Bunge, Judith M. Segall, Gabriel R. Avilucea, Ralph G. Tissot, Mark A. Rodriguez
Tetrahydrofurfuryl alcohol (H-OTHF) was successfully reacted with a series of aluminum alkyls (AlR3) to yield compounds of the general formula [R2Al(μ-OTHF)]2 where R = CH3 (1), CH2CH3 (2), and CH2CH(CH3)2 (3). Further, reactivity studies showed that the alkyls for 1 were easily exchanged, forming compounds of the general formula [Me(OR)Al(μ-OTHF)]2 where OR = OC6H3(Me)2-2,6 (4), OC6H3(CMe3)2-2,6 (5a), and OSi(C6H5)3 (6). For 5a, reflux temperatures were required to get the full exchange; otherwise the asymmetric derivative [Me(OR)Al(μ-OTHF)2AlMe2] (5b) was isolated. The bulk powders of 16 were found to be in agreement with the crystal structures on the basis of elemental analyses and multinuclear solid state NMR studies. Multinuclear solution state NMR studies indicate that the alkyl OTHF derivatives have cis/trans isomers due to the chiral proton on the OTHF ligand.