Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
On the Ring-Opening Reactions of the Furan Compounds. I. The Synthesis of 1,4-Pentadien-3-one-1, 5-dicarboxylic Acid from 2-Furanacrylic Acid
Hiroshi Midorikawa
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1953 Volume 26 Issue 6 Pages 302-304

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Abstract

2-Furanacrylic acid gave 1,4-pentadien-3-one-1,5-dicarboxylic acid in a fairly good yield by treatment with aqueous hydrogen peroxide containing hydrochloric acid. This acid underwent the same photochemical change by direct sunlight as its methyl ester. This acid was reduced to γ-ketopimelic acid hydrazones of the acid by aluminium amalgam, and oxidised to fumaric and oxalic acids by potassium permanganate. It is assumed that the two double bond have the trans structure. The phenyl-hydrazones of the acid and the methyl ester were obtained.

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