SummaryThe application of imidazolinium and amidinium salts as soft Lewis acid organocatalysts is described. These salts were suitable catalysts for the activation of unsaturated thioesters in a Diels–Alder reaction and in the ring opening of thiiranes and epoxides. The products were isolated in good yields. The mild catalysts did not cause desulfurization of the products containing a thiol or thiocarbonyl group.

Tosylated and acetylated imidazolinium salts revealed an unexpected reactivity when treated with methyl iodide or benzyl bromide. Moreover an unprecedented acid-catalysed rearrangement for an acetylated imidazolinium salt was observed during an anion metathesis.

No abstract

Reactions of isonitriles 11a-c with N-(?-aminoalkyl)benzotriazoles 10a-k afford N-(?-aminoimidoyl)benzotriazoles 12a-q which on hydrolysis by dilute hydrochloric acid gave ?-amino amides 14a-j.