Regioselective Synthesis of 2-Hydroperoxy-2-methylenebutanoic Acid Derivatives via Photooxygenation of Tiglic Acid Derivatives
- 1 January 1986
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1986 (12) , 1050-1052
- https://doi.org/10.1055/s-1986-31871
Abstract
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.Keywords
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