We showed in [1] that a-hydroxy thiocyanates can be alkylated by tertiary carbocations, following the Ritter reaction pattern; intermediate thionitrilium cation is stabilized through intramolecular cyclization involving the neighboring hydroxy group to form 2-alkylimino-1, 3- oxathiolanes. With the goal of searching for other functional groups capable of stabilizing thionitrilium cations via intramolecular interaction, we examined the reactions of 1- ...