Our recent study on metallation of isocyanides and its synthetic application has been reviewed. Metallation of isocyanides is achieved by an insertion of isocyanides into metal-metal or metal-carbon linkage of a variety of organometallic compounds giving the corresponding
N-substituted (α-iminoalkyl) metal compounds. The reaction of
N-substituted (α-iminoalkyl) metal compounds thus formed with electrophiles affords the coupled imino compounds, which are transformed to the corresponding ketones by hydrolysis of the imino group. Therefore,
N-substituted (α-iminoalkyl) metal compounds act as acylation equivalents, which permit nucleophilic introduction of the acyl group into organic molecules. A new living polymerization of 1, 2-diisocyanoarenes giving poly (2, 3-quinoxaline) on the basis of the multiple successive insertion of isocyanides is also described.
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