Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Photochemistry of β-Acylacrylic Acids and Their Esters
Noboru SugiyamaHiroshi KataokaChoji KashimaKazutoshi Yamada
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1969 Volume 42 Issue 4 Pages 1098-1100

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Abstract

The irradiation of methyl trans-β-acetylacrylate (I-A) in methanol or acetone or without any solvent gave the cis-isomer (I-B). On the contrary, the irradiation of the free acid of I-A, trans-β-acetylacrylic acid (II-A), in methanol or without any solvent gave the angelica lactone, 5-methyl-5-hydroxy-2-oxo-2,5-dihydrofuran (II-C). The irradiation of trans-β-pivaloylacrylic acid (III-A) in methanol also afforded the angelica lactone, 5-t-butyl-5-hydroxy-2-oxo-2,5-dihydrofuran (III-C). The reaction route from a cis-isomer to an angelica lactone was explained in terms of the inductive effect.

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