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

• Kenta Asahina

  Department of Chemistry, University of Tsukuba

• Junya Asano

  Department of Chemistry, University of Tsukuba

• Gen Kumagai

  Department of Chemistry, University of Tsukuba

• Mitsuru Satou

  Department of Chemistry, University of Tsukuba

• Kouichi Nomoto

  Department of Chemistry, University of Tsukuba

• Yuichiro Kashiyama

  Department of Chemistry, University of Tsukuba

• Hajime Mita

  Department of Life, Environment and Material Science, Fukuoka Institute of Technology

• Shinya Nomoto

  Department of Chemistry, University of Tsukuba

Abstract

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.

Journal

• Chemistry Letters

  Chemistry Letters 39 (12), 1267-1269, 2010-11-06

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360565169064795264
• NII Article ID: 10027468324
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2010.1267
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/39/12/1267/55603399/cl.2010.1267.pdf
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