Oxyfunctionalization of non-natural targets by dioxiranes. 6. On the selective hydroxylation of cubane.
By using methyl(trifluoromethyl)dioxirane (TFDO), the direct mono- and bishydroxylation of cubane could be achieved in high yield under remarkably mild conditions. Comparison of the rates of dioxirane O-insertion with those of standard reference compounds, such as adamantane and cyclopropane, as well as ab initio computations provide useful hints concerning the mechanism of these transformations.
Annese
Cosimo
C
Dipartimento Chimica, CNR.-ICCOM, Università di Bari, v. Amendola 173, I-70126 Bari, Italy.
D'Accolti
Lucia
L
Fusco
Caterina
C
Gandolfi
Remo
R
Eaton
Philip E
PE
Curci
Ruggero
R