Thermolysis of salts of 2-substituted acrylic acids. Novel reduction of a vinyl bromide
Abstract
Upon heating the sodium or silver salts of 2-chloroacrylic, 2-bromo-3,3-diphenylacrylic, and α-bromofluorenylideneacetic acid alone, in inert solvents, or in olefins, decarboxylation results and, where possible, rearrangement to acetylenes. Similarly, methyl fluorenylideneacetates are demethylated and decarboxylated on heating with sodium iodide. These decompositions do not involve carbenes.
Treatment of esters of α-bromofluorenylideneacetic acid with alcoholic alkali or alkoxides causes replacement of bromine by hydrogen, to give fluorenylideneacetic acid in high yield, probably by hydride transfer from the alkoxide ion to the electrophilic double bond.