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. © 1978.
CITATION STYLE
Zitrin, S., Yinon, J., & Mandelbaum, A. (1978). Stereochemistry of retro-diel-salder fragmentation in gas-phase ions formed by chemical ionization. Tetrahedron, 34(8), 1199–1202. https://doi.org/10.1016/0040-4020(78)80145-8
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