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- W2017295835 abstract "A PMR spectroscopic study has been made of the protonation of 1-hexen-5-one (I), 2-methyl-l-hexen-5-one (II), 2-hepten-6-one (III) and 2-methyl-2-hepten-6-one (IV) in different acids (HF, HF-SbF5, H2SO4, FSO3H, FSO3H-SbF5). With two exceptions, the first observable cations were alkyltetrahydrofuryl and/or alkyltetrahydropyryl cations. The cyclizations are very fast. Only in the case of I could the primary “stable” protonation product, the O-protonated ketone, be observed below - 40° in HF. Ketone IV gives a stable dication, C,O-diprotonated IV, in the very strong acid HF-SbF5. The heterocyclic cations derived from I and II are very stable. Those derived from III and IV give subsequent reactions, namely simple interconversion of five and six-membered heterocyclic rings, skeleton isomerizations proceeding via acyclic dications, and in the case of the ions derived from IV the eventual formation of 1,3-dimethylcyclohexenyl ion. The rates of all transformation reactions and the ratios of the products formed were found to depend strongly on the acid used. In the case of the skeleton isomerizations the rates depend on the acidity of the solvent (HF-SbF5〉〉FSO3-SbF5〉〉〉HF, H2SO4, FSO3H). For the other types of reactions the rates strongly vary with the type of solvent (HF versus H2SO4 or FSO3H)." @default.
- W2017295835 created "2016-06-24" @default.
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- W2017295835 date "2010-09-02" @default.
- W2017295835 modified "2023-09-23" @default.
- W2017295835 title "Alkyltetrahydrofuryl and -pyryl cations: Formation by cyclization of protonated alkenones and transformations in different acids" @default.
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- W2017295835 doi "https://doi.org/10.1002/recl.19690880504" @default.
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