Synthesis of 1,3-dioxin-4-ones and their use in synthesis. XIII Synthesis of 5-halo-1,3-dioxin-4-ones and their conversion to 5-alkyl derivatives.

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Abstract
A novel method for the introduction of an alkyl group at the 5-position of 1, 3-dioxin-4-ones is described. Reaction of 5, 6-unsubstituted 1, 3-dioxin-4-ones with N-halosuccinimide in acetic acid followed by treatment with a base gave 5-bromo- and 5-iodo-1, 3-dioxin-4-ones, which were converted to the corresponding 5-alkylated dioxinones either by palladium-catalyzed cross-coupling or by photochemical allylation reactions. Successful conversion of 5-ethyl-2, 2-dimethyl-1, 3-dioxin-4-one either to a 5-ethyl-1, 3-oxazin-4-one derivative or an α-ethylformylacetate upon heating in xylene demonstrated that these 5-substituted 1, 3-dioxin-4-ones can serve as chemical equivalents for substituted formylketenes.

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