Journal of Organic Chemistry p. 1078 - 1082 (1988)
Update date:2022-08-03
Topics:
Bloodworth, A. J.
Melvin, T.
Mitchell, John C.
Monocyclic gem-dialkylperoxonium ion 2 has been generated from the reaction of 1-bromo-4-hydroperoxy-4-methylpentane (1) with silver tetrafluoroborate or trifluoroacetate, and related bicyclic ion 4 has been formed from the reaction of 5-hydroxyperoxycyclooctene (3) with N-bromosuccinimide.These species have been shown to oxidize efficiently both dialkyl sulfoxides and methyl phenyl sulfide.Reaction with thianthrene 5-oxide afforded XNu values of 0.10 for 2 and 0.72 for 4, while competition reactions with (p-XC6H4)2SO (X=Me, H, F, and Cl) yielded Hammett ρ values (versus ?) of -0.83+/-0.11 and -1.77+/-0.58.These results indicate that gem-dialkylperoxonium ion salts,R2O+-OH,X-, are electrophilic oxygen transfer reagents, tunable to some extent by choice of R1, R2, and X, but provide no evidence of deprotonation to the corresponding dioxygen ylide under the conditions studied.
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