Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 10. Reactions of s-Alkyl Primary Amines with Pyryliums

Article abstract of DOI:10.1039/P29830001435

2,4,6-Triphenylpyrylium with s-alkylamines gives isolatable pyridiniums (which undergo S_N2 substitution with nucleophiles and elimination to olefins). 2,4,6-triphenylpyrilium with 1-phenylethylamine and α-phenylbenzylamine forms the corresponding carbonium ions which may be trapped by nucleophiles.Isolated 1-cycloalkylbenzoquinoliniums (2) solvolyse by the S_N1 mechanism (for five-, six- and seven-membered rings): for the cyclobutyl case an S_n2 reaction is also found.