THE LOSS OF AMINE FROM ELECTRON IONIZED LARGE-RING CYCLOALKYLAMINES

Large-ring ionized cycloalkylamines of low internal energy lose ammoni a and homologous alkyl radicals competitively. It is shown by deuteriu m-labelling experiments, that ammonia is lost mainly after ring-contra ction of the original parent ion to an alkyl-monosubstituted cyclohexy lamine isomer. This fragmentation is preceded by abundant hydrogen exc hanges occurring mainly in this rearranged structure, but also, for th e largest ring compounds, to some extent in the original structure.