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A McLafferty rearrangement in an even‐electron system: C 3 H 6 elimination from the α‐cleavage product of tri‐ n ‐butylamine

1991; Wiley; Volume: 26; Issue: 8 Linguagem: Inglês

10.1002/oms.1210260808

2376-3884

H. Budzikiewicz, Peter Bold,

Spectroscopy and Quantum Chemical Studies

Abstract It is shown by deuterium labelling, linked‐scan measurements and collision activation that the [M‐C 3 H 7 ˙] + (α‐cleavage) ion in the electron impact ionization spectrum of tributylamine loses C 3 H 6 with transfer of one hydrogen specifically from the γ‐position. The experimental data point towards a mechanism which involves the intermediate formation of a distonic diradical ion from an excited α‐cleavage ion which then eliminates the neutral alkene.