Substituted polycycloalkylidenepolycycloalkanes and the corresponding epidioxy compounds

Polycycloalkylidenepolycycloalkanes were halogenated using N-halosuccinimide, tert-Bu hypohalite, or sodium hypohalite-AcOH, and optionally substituted. Thus adamantylideneadamantane (I, R = H) was treated with N-bromosuccinimide to give I (R = Br) (II) which was treated with HOAc to give I (R = OAc). II underwent photooxygenation to give the epidioxyadamantyladamantane III. Epidioxyadamantyladamantes may be used as thermochemiluminescent labels in biol. processes and immunoassays (no data). [on SciFinder (R)]