Progress on the Synthesis of Facially Hindered Metallobenzporphyrins
Abstract
Reaction of isoindole, benzaldehyde and zinc acetate at 400 C has been shown to be a useful synthesis of zinc meso-tetraphenyltetrabenzporphyrin. We have repeated this reaction using mesitaldehyde (2,4,6-trimethylbenzadehyde) in place of benzaldehyde. Proton NMR analysis of the product indicates that only partial substitution of mesityl groups in the meso positions has occurred. This is contrasted with the reaction of pyrrole and mesitaldehyde in the presence of boron trifluoride etherate followed by treatment with chloranil to yield meso-tetramesitylporphyrin. Attempts to extend this synthesis to the tetrabenzporphyrins by using isoindole in place of pyrrole were unsuccessful. Keywords: Porphyrins, Tetrabenzporphyrins, Meso-substituted porphyrins, Synthesis, NMR spectroscopy.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jul 12, 1988
- Accession Number
- ADA198784
Entities
People
- D. E. Remy
- J. W. Cullen
Organizations
- United States Army Soldier Systems Center