The First Experimental Demonstration of Side Chain Extension of Geoporphyrins in Sediments

To investigate the formation process of high carbon number (>C32) sedimentary porphyrins, heating experiments of several porphyrins were performed. Chromic acid oxidation of the heating products of protoporphyrin IX dimethyl ester afforded 2-methyl-3-n-propylmaleimide as the predominant product a...

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Bibliographic Details
Published in:Chemistry letters 2010-12, Vol.39 (12), p.1267-1269
Main Authors: Asahina, Kenta, Asano, Junya, Kumagai, Gen, Satou, Mitsuru, Nomoto, Kouichi, Kashiyama, Yuichiro, Mita, Hajime, Nomoto, Shinya
Format: Article
Language:English
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Summary:To investigate the formation process of high carbon number (>C32) sedimentary porphyrins, heating experiments of several porphyrins were performed. Chromic acid oxidation of the heating products of protoporphyrin IX dimethyl ester afforded 2-methyl-3-n-propylmaleimide as the predominant product among the side-chain extension products formed. On the other hand, saturated substituents of etioporphyrin were also extended on heating to slowly form normal and branched homologs. These results may suggest that the transalkylation of porphyrin side chains proceeds mainly by a regioselective mechanism involving alkyl radical addition to a vinyl group of chlorophylls or their diagenetic products.
ISSN:0366-7022
1348-0715
1348-0715
DOI:10.1246/cl.2010.1267