Asmic
Anisyl sulfanyl methyl isocyanide is an organic compound with the formula. The molecule contains an ortho-methoxy-phenyl sulfide group to which is attached the isocyanide. Asmic is used as a reagent for the synthesis of tri-substituted isocyanides. The compound is a colorless although samples can appear off-white.
Preparation and reactions
Asmic is prepared by dehydration of the corresponding formamide by POCl3.Asmic can be deprotonated at the methylene adjacent to the isocyanide. The anionic form of Asmic, which is stable at low temperatures, can be alkylated with a variety of electrophiles. Two sequential deprotonation-alkylation reactions and a subsequent sulfur-lithium exchange reaction allow the synthesis of tri-substituted isocyanides.
The ortho-methoxy-phenyl sulfide group is thought to facilitate deprotonation by chelating to metalated bases allowing for the base to achieve optimal trajectory during the deprotonation.
Asmic can be used to prepare oxazoles by condensation reactions with esters. The ortho-methoxy-phenyl sulfide group can also undergo sulfur-lithium exchange, and likely proceeds via a 10-s-3 sulfuranide.