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Using deuterium labelled compounds the mechanisms of methyl as well as methanol elimination from the title compounds have been established. It can be shown that in the case of 4-methoxy-methyl benzoic acid methyl ester the unusual methanol elimination from the [M-methyl]+ ion probably proceeds via the formation of a π-complex and a ring expansion reaction. In addition to this novel fragmentation some ortho-effects and other fragmentation reactions useful for an analytical identification of the ortho/para-isomers by means of mass spectrometry are discussed.

zeitschrift für naturforschung b

Mechanismen der elektronenstoßinduzierten Methanoleliminierung aus ortho- und para-substituierten Benzoesäuremethylestern / Mechanisms of Electron Impact Induced Elimination of Methanol from ortho- and para-Substituted Benzoic Acid Methyl Ester