Beitrag zum Mechanismus der stossinduzierten Fragmentierungen von quaternären Stickstoffverbindungen. 2. Mitteilung über stossinduzierte Fragmentierungen von felddesorbierten Kationen

Abstract

Mechanistic studies on the collision‐induced fragmentations of quaternary ammonium ionsThe collision‐induced fragmentation behaviour of field desorbed quarternary ammonium ions has been investigated. A main reaction of these ions is the cleavage of the NC bond accompanied by hydrogen rearrangement, i.e. alkane loss from the tetraalkyl substituted ammonium ions of the iodides 1, 2 and 3, respectively, Deuterium labelling indicates that the hydrogen transfer to the leaving group occurs to the extent of about 80% from the α‐position and about 20% from the other positions of an alkyl group. Pronounced heterolytic cleavage of the NC bond is observed in the benzyl substituted ammonium ion of 4. The β‐phenylethyl substituted ammonium ion of 5 shows a homobenzylic heterolysis, possibly yielding the phenonium ion j.