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Abstract
Various 2,3-dihydro-2-substituted-2-vinyl-1,4-benzodioxins 6 are obtained by alkylation of the methyl carbonate of 2,3-dihydro-1,4-benzodioxin-2-ylideneethanol 5 with various carbon nucleophiles in the presence of a palladium complex. Altough the yields in alkytion products are good in the case of a non-bulky nucleophile, formation of the diene 7 was generally observed when a bulky nucleophile was used.
Highlights
Compounds containing 1,4-benzodioxin and 1,4-benzodioxan structures have attracted considerable interest in recent years
Various 2,3-dihydro-2-substituted-2-vinyl-1,4-benzodioxins 6 are obtained by alkylation of the methyl carbonate of 2,3-dihydro-1,4-benzodioxin-2-ylideneethanol 5 with various carbon nucleophiles in the presence of a palladium complex
We have recently described the preparation of various 2,3-dihydro-2ylidene-1,4-benzodioxins via a palladium–catalyzed condensation of benzene-1,2-diol with different propargylic carbonates.[22]
Summary
Compounds containing 1,4-benzodioxin and 1,4-benzodioxan structures have attracted considerable interest in recent years. Dimethyl malonate (Table 1, entry 1) and acetylacetone (Table 1, entry 2) reacted with carbonate 5 to give after column chromatography the alkylated 2,3-dihydro-2-vinyl-benzo-1,4dioxins 6a and 6b in 67 and 53% yield, respectively.
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