The Reaction of Isocyanides with Halogens or N-Halosuccinimides and Alcohols

Article abstract of DOI:10.1246/bcsj.55.2480

The reaction of aliphatic isocyanides with bromine or chlorine in primary alcohols, followed by hydrolysis, afforded the corresponding carbamates in moderate yields, together with various amounts of amines.Bromine was superior to chlorine as a halogen source for the formation of carbamates, unexpectedly, the addition of HgCl2 resulted in a decrease in the carbamate yield.When N-halosuccinimides were used in the place of halogens, an additional formation of the succinimide-incorporated product was observed to some extent.