Journal of the Chemical Society. Perkin transactions II p. 281 - 284 (1983)
Update date:2022-08-11
Topics:
Dallinga, Jan W.
Nibbering, Nico M. M.
Boerboom, A. J. Henk
It is shown by tandem mass spectrometry that Curie point pyrolysis of but-3-ynoic and buta-2,3-dienoic acid leads to the formation of propyne.This points to a thermodynamically controlled elimination of carbon dioxide which for both acids can be rationalized by a combined 1,4- and 1,2-hydrogen shift of the hydroxylic hydrogen atom.The C3H4(1+). ions, generated upon electron impact induced decarboxylation of the molecular ions of but-3-ynoic and buta-2,3-dienoic acid, have been shown by tandem mass spectrometry to have the allene and propyne structure, respectively.Their formation can be explained by a 1,5-hydrogen shift of the hydroxylic hydrogen atom prior to or during the loss of carbon dioxide from the molecular ions.
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