Mass spectra of alkylquinolines

A study has been made of the fragmentation upon electron impact of monomethylquinolines, di-methylquinolines, monoethylquinolines, and monopropylquinolines. Deuterium labelled analogues of some of the alkylquinolines have been prepared and their fragmentation studied to gain insight into the mechanism of fragmentation. The fragmentation of the alkylquinolines is closely analogous to that of alkylbenzenes. Rearrangement of the molecular ion appears to precede the fragmentation process in many of the compounds studied. The fragmentation of 2- and 8-ethyl- and n-propylquinolines are influenced by the proximity of their alkyl side chains to the nitrogen atom.