OXIDATIVE FUNCTIONALIZATION OF UNACTIVATED CARBON-HYDROGEN BONDS IN 0(2,6).0(3,13).0(4,11).0(5,9).0(10,14)]TETRADECANE (HCTD)

Gif-type reactions have been used to perform direct oxidative function alization of the title compound (HCTD, 1). Thus, GoAgg(III) and GoAgg( IV) promoted oxidations of 1 afford (2,6).0(3,13).0(4,11).0(5,9)-.0(10 ,14)]tetradecane [i.e., 1-(2'-pyridyl)HCTD, 2] in 6-10% isolated yield . In addition to 2, GoAgg(V) promoted oxidation of 1 produced ).0(3,13 ).0(4,11).0(5,9).0(10,14)]tetradecan-7-one (HCTD-3-one, 3) and 1-(4'-p yridyl)HCTD (4) in low isolated yield. Finally, oxidation of 1 perform ed by using an Fe-II-t-BuOOH system afforded several products, includi ng ,6).0(3,13).0(4,11).0(5,9)]tetradecane-10,14-dione (6) and 0,0(2,6) .0(3,13).0(4,11).0(5,9)]-tetradecan-10-one (7), both of which resulted via oxidative cleavage of the C(1)-C(2) sigma-bond in 1. (C) 1997, El sevier Science Ltd.