THE SELECTIVE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .28. THE ACTIVATION OF BENZYLIC METHYLENE GROUPS UNDER GOAGG(IV) AND GOAGG(V) CONDITIONS

Under GoAgg(IV) and GoAgg(V) conditions, cyclohexadienes were oxidized to give aromatic products instead of ketones and alcohols. At the same time, anthracene was oxidized to give anthraquinone. Under GoAgg(IV) and GoAgg(V) conditions, xanthene, fluorene and diphenylmethane were oxidized to give the corresponding xanthone, fluorenone and benzophenone following two possible pathways: a) alkane to alkyl t-butylperoxide to ketone, and b) alkane to ketone, in which alkyl hydroperoxide, derived from oxygen, may be the reaction intermediate. Xanthyl azide was farmed when sodium azide was added to the reaction mixture of xanthene under GoAgg(IV) and GaAgg(V) conditions. The reaction of triphenylmethane under GoAgg(V) conditions gave triphenylmethyl t-butyl peroxide as the major product and hydroperoxide as the minor product. When TEMPO was added, triphenylmethyl hydroperoxide was the only product.