Anisyl sulfanyl methyl isocyanide (Asmic) is an organic molecule that contains an isocyanide group and an ''ortho-''methoxy-phenyl

sulfide Sulfide (British English also sulphide) is an inorganic anion of sulfur with the chemical formula S2− or a compound containing one or more S2− ions. Solutions of sulfide salts are corrosive. ''Sulfide'' also refers to chemical compounds lar ...

group. Asmic can be used to synthesize tri-substituted isocyanides. Asmic is a colorless to off-white solid with a melting point of 27 °C that can be prepared by dehydration of the corresponding formamide by POCl₃. Asmic can be deprotonated at the position adjacent to the isocyanide by various

organic bases An organic base is an organic compound which acts as a base. Organic bases are usually, but not always, proton acceptors. They usually contain nitrogen atoms, which can easily be protonated. For example, amines or nitrogen-containing heterocyclic ...

. 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.

References

{{reflist Thioethers Isocyanides