The mass spectrum of exo-2-norbornyl chloride; the elucidation of the fragmentation mechanism and ion structures by metastable ion analysis

Abstract

The mass spectra of exo-2-norbornyl chloride and several deuterated analogues have been examined in detail with particular regard to metastable peaks involving the molecular ions and norbornyl cations. The molecular ion does not undergo Wagner–Meerwein isomerization prior to fragmentation; in the norbornyl cation the hydrogen atoms have lost their identity as shown by random H and D loss when the ion ejects an ethylene molecule. Metastable ion analysis is proposed as a method for studying the participation of norbornyl carbonium ions in the preparation of 2-norbornyl chloride.