Syntheses of per-N labeled etioporphyrins I-IV and a related tetrahydrobenzoporphyrin for applications in organic geochemistry and vibrational spectroscopy |
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Authors: | Timothy D. Lash Shaohua Chen |
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Affiliation: | Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA |
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Abstract: | Nitrogen-15 labeled pyrroles have been prepared from commercially available 15N glycine or sodium nitrite using the Barton-Zard, Knorr, and Kleinspehn approaches. These pyrroles were used as intermediates in the synthesis of per-15N labeled porphyrins needed for the analysis and assignment of vibrational spectra for sedimentary porphyrins. Etioporphyrin-I was prepared via pyrromethene intermediates, while etioporphyrins II-V and a related tetrahydrobenzoporphyrin were synthesized via stepwise routes involving the copper(II) mediated cyclization of a,c-biladienes as the key step. Detailed analyses of both the proton and carbon-13 NMR spectra provide nitrogen-15 coupling constants for these important structures. |
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Keywords: | Pyrroles Nitrogen-15 NMR spectroscopy Petroporphyrins Organic geochemistry |
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