Electron impact induced fragmentation of alkyl(benzylidene)amines
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 854-861
- https://doi.org/10.1039/p29730000854
Abstract
The mass spectral decomposition reactions of alkyl(benzylidene)amines (Schiff's bases) have been investigated with the aid of deuterium labelling, high resolution measurements, and metastable defocusing. The most significant results are (a) cleavage of the C(4)–C(5) bond (δ-cleavage) with formation of five-membered ring fragment ions is very much favoured over other C–C bond fissions; (b) very abundant C7H7 + ions are formed through skeletal rearrangement processes, joining the phenyl group to the α-methylene group of the alkyl fragment; and (c) very abundant (M–C6H5) and (M–C6H6) ions are formed at low voltage from benzylidene(butyl)amine and the labelled analogues, the C6H6 neutral fragment eliminated incorporating the methine hydrogen atom. Ring closure is suggested to accompany the formation of both ions; similar fragmentations take place to a much lesser extent in the fragmentation of other alkylimines.Keywords
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