Chemical synthesis study demonstrates n-BuLi-induced rearrangement of bromoarylacrylonitriles into o-cyanoarylacetylenes, highlighting a versatile route to functionalized alkynes.
A novel unexpected anionic domino process involving n-BuLi-induced rearrangement of 3,3-bis(methylthio) or 3-methylthio-3-aryl/heteroaryl/alkyl-o-bromoarylacrylonitriles to o-cyanoarylacetylenes in synthetically useful yields has been reported. The scope and generality of the reaction has been examined, and a possible mechanism has been proposed.
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Kumar et al. (2008) studied this question.
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