Stereochemistry of retro-diel-salder fragmentation in gas-phase ions formed by chemical ionization |
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| Authors: | Shmuel Zitrin Jehuda Yinon Asher Mandelbaum |
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| Affiliation: | 1. Department of Isotope Research, The Weizmann Institute of Science, Rehovot, Israel;2. Department of Chemistry, Technion-lsrael Institute of Technology, Haifa, Israel |
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| Abstract: | Retro Diels Alder fragmentation is highly stereospecific in the diones 1 under chemical ionization conditions, both with methane and isobutane as the reagent gases. Only the cis-isomers yield abundant protonated diene and quinone ions. The isotope effect indicates preferential protonation on a CO oxygen, and a subsequent H-migration prior to the formation of the protonated diene cations in the cis isomers. |
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