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- W2065408090 abstract "Base-catalyzed H/D-exchange for α- and β-isophorone (1 and 2, resp.) was monitored by NMR spectroscopy to identify the number and nature of reactive sites. Results show that α-isophorone (1) undergoes H/D exchange at up to four different sites depending on reaction conditions. β-Isophorone (2), on the other hand, exhibits activity at two sites, predominantly at the α-position, under comparable conditions. Quantum-chemical calculations indicate that the thermodynamically more-stable anions formed upon proton abstraction from isophorone are not favored kinetically in all cases. Thermodynamically unfavorable H/D-exchange at the α-position in 1, which is observed experimentally, is explained via intermediate formation of γ-isophorone (3) with subsequent conjugation to the α-isomer. Differences observed in the reactivities of the two isomers and differences in reactivity of 1 under various conditions in reactions involving proton abstraction as an initial step may be partly explained on the basis of these results." @default.
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- W2065408090 date "2001-10-17" @default.
- W2065408090 modified "2023-09-23" @default.
- W2065408090 title "Reactive Sites in Isophorone Isomers: H/D-Exchange Studies and Quantum-Chemical Calculations" @default.
- W2065408090 doi "https://doi.org/10.1002/1522-2675(20011017)84:10<2884::aid-hlca2884>3.0.co;2-8" @default.
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