Pyrylium-Mediated Conversion of Primary Alkyl Primary Amines into Olefins via Tetrahydrobenzoacridiniums: A Mild Alternative to the Hofmann Elimination

Article abstract of DOI:10.1021/jo00139a024

Primary alkyl primary amines react with the pentacyclic pyrylium 2 to give the corresponding pyridiniums which thermolyze at 150-180 deg C into the olefins in high yield.The terminal olefins are accompanied by cis- and trans-2-olefinic isomers: proportions are elucidated by GLC and advantageously by 13C NMR spectroscopy, combining gated decoupling and (acac)3Cr^III.