Bis(trimethylsilyl) peroxide (1)
functions as an electrophilic hydroxylating agent for aliphatic,
aromatic, and heteroaromatic anions.Reaction of their lithium
or Grignard compounds with (1) often affords trimethylsiloxy
intermediates, which undergo desilylation with HCl in methanol
to give the corresponding alcohols in good yields. In the presence
of a catalytic amount of trifluoromethanesulfonic acid, (1)
reacts with aromatic compounds to produce the corresponding
phenols after acidic workup.In these reactions the Me3SiO?
moiety is considered as a synthon of the hydroxyl cation
(i.e. OH+).
