Fragmentation mechanism of rose oxide in electron impact mass spectrometry

Eur. J. Mass Spectrom. 4, 163–166 (1998)
DOI: 10.1255/ejms.204

Fragmentation mechanism of rose oxide in electron impact mass spectrometry

Matthias Wüst, Sabine Fuchs, Annette Rexroth, Thomas Beck and Armin Mosandl^*
Institut für Lebensmittelchemie, Biozentrum, Johann Wolfgang Goethe-Universität, Marie-Curie Str. 9, D-60439 Frankfurt, Germany. E-mail: Mosandl@em.uni-frankfurt.de.

ABSTRACT:

The fragmentation mechanism of cis/trans-rose oxide (1,2) in mass spectrometry is investigated using specifically deuterium labeled isotopomers. The main fragmentation pathway is not initiated by the loss of the 4-methyl group as previously assumed. The labeling experiments are in agreement with a fragmentation mechanism which includes a hydrogen rearrangement of H-2 and the loss of one of the methyl groups of the isopropylidene substituent.

Keywords: Rose oxide, 2-(2-methyl-1-propenyl)-4-methyltetrahydropyran, deuterium labeling, oxygen-18 labeling, electron impact mass spectrometry, fragmentation mechanism

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