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Synthesis 1986; 1986(12): 1050-1052
DOI: 10.1055/s-1986-31871
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Regioselective Synthesis of 2-Hydroperoxy-2-methylenebutanoic Acid Derivatives via Photooxygenation of Tiglic Acid Derivatives

Waldemar Adam* , Axel Griesbeck
  • *Institut für Organische Chemie der Universität Würzburg, Am Hubland D-8700 Würzburg, West Germany
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Publication Date:
12 September 2002 (online)

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Photooxygenation of (E)-2-methyl-2-butenoic acid derivatives (tiglic acid derivatives) in tetrachloromethane in the presence of catalytic amounts of tetraphenylporphine affords 3-hydroperoxy-2-methylenebutanoic derivatives in generally high yields. Acid-catalyzed cyclodehydration of the 3-hydroperoxy-2-methylenebutanoic acid thus obtained readily gives 5-methyl-4-methylene-3-oxo-1,2-dioxolane, a peroxylactone, in 61% yield. The analogous cyclodehydration of 3-hydroperoxy-2-methylenebutanal [generated in situ by oxygenation of (E)-2-methyl-2-butenal] leads to the formation of 3-hydroxy-5-methyl-4-methylene-1, 2-dioxolane.