• Synthetic experiments in the benzo-pyrone series - Part VI. Action of aluminium chloride on angelicin, psoralen and related compounds

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      https://www.ias.ac.in/article/fulltext/seca/016/02/0151-0156

    • Keywords

       

      Coumarin; Nitrobenzene; Aluminium Chloride; Methyl Ether; Psoralen

    • Abstract

       

      Angelicin and psoralen combine with benzene in the presence of aluminium chloride to form 8 or 6-α: β-diphenyl-ethylumbelliferone. Two molecules of benzene add on and the furan ring is opened out. That the coumarin ring is not involved and that the furan ring is the active centre are confirmed by the following observations: (1) Coumarin and 6-nitrocoumarin are unaffected; (2) umbelliferone and 4-methyl-umbelliferone methyl ether undergo simple demethylation; (3) coumarone undergoes polymerisation too vigorously to condense with benzene; (4) coumarilic acid undergoes addition with one molecule of benzene smoothly. Coumaric acid resembles coumarilic acid in regard to this reaction (addition) and differs from coumarin.

    • Author Affiliations

       

      B Krishnaswamy1 T R Seshadri1

      1. Department of Chemistry, Andhra University, Waltair
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