HX-Eliminierung (X = OH, NH2) aus primären ω-phenylsubstituierten Alkoholen und Aminen: Indiz für interne Solvatisierung von Radikalkationen in der Gasphase oder Resultat einer selektiven Aktivierung von CH-Bindungen? / HX-Elimination (X = OH, NH2) from Primary ω-Phenylsubstituted Alcohols and Amines: a Probe for Internal Solvation of Gaseous Radical Cations or the Result of a Selective Activation of CH-Bonds ?

Abstract

Using collisional activation mass spectrometry the structures of the [M–HX]+• ions (X = OH, NH2) from 5-phenylpentanol-1 (1), 5-phenylpentylamine (2) and 6-phenylhexanol-1 (3) have been established. Contrary to previous results it is shown for the first time that in addition to ionized 1-phenyl-alkenes-1 some other double bound isomers as well as phenylcyclopentane and phenylcyclohexane are formed. The results strongly suggest that the HX eliminations are induced by a selective activation of CH bonds.