CARBON TRANSFER REACTIONS OF Δ2-OXAZOLINIUM AND THIAZOLINIUM CATIONS

Article abstract of DOI:10.1016/S0040-4020(01)87364-6

Δ²-Oxazolinium and thiazolinium cations with or without an appendage at any of the heteroatoms transfer their C(2) units at the carboxylic acid oxidation level to binucleophiles and provide the corresponding heterocycles, thus mimicking carbon transfer reactions exhibited by THF models, N-methyl N'-tosyl/acetyl imidazolinium cations.However, these azolinium cations react with phenethylamine and tryptamine to furnish their N-acyl derivatives.