The exhaustive reduction of formylporphyrins to methylporphyrins using dimethylformamide/water as reductant under microwave irradiation
Fletcher, Sarah, Harper, Shannon, & Arnold, Dennis (2014) The exhaustive reduction of formylporphyrins to methylporphyrins using dimethylformamide/water as reductant under microwave irradiation. Journal of Porphyrins and Phthalocyanines, 18(3), pp. 200-208.
The reduction of meso-formyl derivatives of 5,15-diaryl- and 5,10,15-triphenylporphyrin (and their nickel(II) complexes) to the corresponding meso-methyl porphyrins is achieved in high yield by microwave heating of the substrate in dimethylformamide (DMF) in the presence of acids such as trifluoroacetic acid, or even just with added water. The reactions are complete in less than 30 min at 250 °C. The reaction is strongly suppressed in very dry DMF in the absence of added acid. The meso-hydroxymethyl porphyrins are also reduced to the methyl derivatives, suggesting the primary alcohols may be intermediates in the exhaustive reduction. UV-visible spectra taken at intervals during reaction at 240 °C indicated that at least one other intermediate is present, but it was not identified. In d7-DMF, the methylporphyrin isolated was mainly Por-CD2H, showing that both of the added hydrogens arise from the solvent, and not from the added water or acid.
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|Item Type:||Journal Article|
|Keywords:||dimethylformamide, formylporphyrins, methylporphyrins, microwave, reduction|
|Divisions:||Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
|Copyright Owner:||Copyright 2014 World Scientific Publishing Co. Pte. Ltd.|
|Deposited On:||02 Nov 2015 02:18|
|Last Modified:||02 Nov 2015 02:18|
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