Acylation of arsenic β-ketoylides by carboxylic acid halides
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In contrast to the corresponding phosphorus ylide, triphenylarsinebenzoylmethylene is acylated by acyl bromides at two reaction centers: at the O and C atoms. Triphenylarsineacetylmethylene gives only an O-acylation product.
In contrast to the phosphorus analogs, acyloxyvinylarsonium salts rearrange on heating into the C-acylated analogs.
During rearrangement of β-substituted benzoyloxyvinyltriphenylarsoriium bromides in the presence of sodium acetate and β-substituted acetoxyvinyltriphenylarsonium bromides in the presence of sodium benzoate, one and the same mixture of diacyl ylides is formed. It was shown that the rearrangement proceeds via the stage of splitting of the acyl group, followed by C-acylation of the ylide formed by an anhydride.
KeywordsSodium Acetate Phosphorus Bromide Arsenic
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