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The electron ionization (EI) mass spectra of some new bridgehead 7,7-dimethylnorbornane-based β-amino alcohols have been studied and their fragmentation patterns compared with those of isomeric 3,3-dimethyl derivatives described by us previously. The dimethyl substitution at C7 results in a significant complication of the spectra, although all compounds show a C1–C2 bond cleavage with charge location at the nitrogen atom that leads to the base peak. Thus, two main fragmentation patterns dominated by cyclopentenylimmonium or methyleneimmonium ions are described depending on the position of the amino group in the norbornane framework (C1 or C2, respectively), as well as other secondary routes that can explain the appearance of the less noticeable fragments. Copyright © 2005 John Wiley & Sons, Ltd.

The electron impact mass spectra of several 3,3-dimethyl-1, 2-norbornanediols, diamines, amino alcohols and related derivatives have been studied and their fragmentation pathways discussed. Different fragmentation patterns were observed, depending not only on the nature of the substituents, but also on their relative positions on the norbornane framework. In general, the dominant peaks in the spectra of these compounds originate from initial C1-C2 bond cleavage (alpha-cleavage) with charge retention on the heteroatom (oxygen or nitrogen) attached at the bridgehead position, followed by hydride shift and loss of the C2-C3 fragment by homolytic cleavage of the C3-C4 bond. This fragmentation pathway leads to a highly stabilized cyclopentenylimmonium or cyclopentenyloxonium ion, which constitutes the base peak in the spectra in most of the studied compounds. Copyright 1999 John Wiley & Sons, Ltd.