p-Toluenesulfonylmethyl isocyanide is a synthetic reagent used in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton, pyrroles, oxazoles and in imidazoles. It serves as an isonitrile component in a diastereoselective Passerini reaction. Furthermore, it is used in the Van Leusen reaction to convert aldehydes to nitriles.
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Applications
p-Toluenesulfonylmethyl isocyanide is a synthetic reagent used in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton, pyrroles, oxazoles and in imidazoles. It serves as an isonitrile component in a diastereoselective Passerini reaction. Furthermore, it is used in the Van Leusen reaction to convert aldehydes to nitriles.
Solubility
Soluble in chloroform and methanol. Insoluble in water.
Notes
Moisture, air and light sensitive. Store in cool place. Incompatible with strong bases and strong oxidizing agents.
RUO – Research Use Only
General References:
- Successive alkylation with different alkyl groups, followed by acid hydrolysis, leads to unsymmetrical ketones: Tetrahedron Lett., 4229 (1977). Similarly, dialkylation with ɑω-dihalides gives cyclobutanones: Synthesis, 325 (1980), or larger-ring ketones: Tetrahedron Lett., 22, 4193 (1981). Reaction of monoalkylated TosMIC with ɑω-dihalides is a useful route to 1,5- or 1,6-diketones: Rec. Trav. Chim., 104, 50 (1985):
- In the presence of base (e.g. KO-t-Bu) in an aprotic solvent, e.g. DME, ketones are cyanated to give the homologous nitriles; see, e.g.: Org. Synth. Coll., 6, 41 (1988). Hindered ketones can be cyanated in DMSO: J. Org. Chem., 42, 3114 (1977). Aldehydes condense with TosMIC at -50o, followed by hydrolysis in refluxing methanol: Synth. Commun., 10, 399 (1980).
- In contrast, aldehydes with K2CO3 in refluxing methanol lead to high yields of 5-substituted oxazoles: Tetrahedron Lett., 2369 (1972); with acid chlorides, the corresponding 4-tosyl oxazoles are obtained. For asymmetric induction in the oxazole synthesis by use of π-arylaldehyde-chromium tricarbonyl complexes, see: Tetrahedron: Asymmetry, 3, 287 (1992).
- Other applications in heterocyclic synthesis include the synthesis of: