|Preferred IUPAC name
Asmic; Anisyl sulfanyl methyl isocyanide
3D model (JSmol)
|Molar mass||179.24 g·mol−1|
|Melting point||27 °C (81 °F; 300 K)|
|Solubility in polar organic solvents||Soluble|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Anisyl sulfanyl methyl isocyanide (Asmic) is an organic molecule that contains an isocyanide group and an ortho-methoxy-phenyl sulfide 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. 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.
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.
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- Abstracts of Papers, 256th ACS National Meeting & Exposition, Boston, MA, United States, August 19-23, 2018 ASMIC-driven synthesis of vinyl isocyanide
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