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Evidence for a [2+4] cycloaddition in the ion‐molecule reaction of ionized 1,3‐butadiene with vinyl ethyl (methyl) ether in the gas phase
Author(s) -
Van Doorn R.,
Nibbering N. M. M.,
FerrerCorreia A. J. V.,
Jennings K. R.
Publication year - 1978
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210131212
Subject(s) - electron ionization , chemistry , cycloaddition , ether , ion , polyatomic ion , molecule , mass spectrum , excited state , ionization , photochemistry , deuterium , medicinal chemistry , cyclohexene , organic chemistry , atomic physics , physics , catalysis
By use of deuterium labelling it is shown that the radical cation of 1,3‐butadiene reacts with vinyl methyl (or ethyl) ether in the gas phase through a [2+4] cycloaddition reaction. This leads to an excited collision complex of ionized 4‐methoxy‐ (or ethoxy) cyclohexene, which expels mthanol (or ethanol) through a 1,3 elimination, as does 4‐methoxycyclohexene itself upon electron impact. The spectrum of daughter ions produced by collision induced decomposition of the resulting ion with m / e 80 has been compared with spectra produced by the collision induced decompositions of the m / e 80 ions given by 1,3‐cyclohexadiene, 1,4‐cyclohexadiene, 1,3,5‐hexatriene and the [M–MeOH] \documentclass{article}\pagestyle{empty}\begin{document}$\mathop +\limits_\cdot$\end{document} ion from 4‐methoxycyclohexene.