Nucleophilic displacement with heterocycles as leaving groups. Part 16. Reactions of secondary alkyl primary amines with 5,6,8,9-tetrahydro-7-phenyldibenzo[c,h]xanthylium trifluoromethanesulphonate to give intermediates solvolysing without rearrangement

Abstract

Representative secondary alkyl primary amines R¹ R²CHNH₂ react with the title pyrylium cation in acetic acid, alcohols, phenols, and NN-dimethylaniline acting as nucleophilic solvents to give O- and C-(secondary alkyl) products. Absence of carbenium ion rearrangements is consistent with reaction via intimate ion–molecule pairs formed rapidly from the corresponding pyridinium cations.