Naslov
Oxidative functionalizaion of unactivated carbon-hydrogen bonds in heptacyclo[6.6.0.02, 6.03, 13.04, 11.05, 9-.010, 14]tetradecane (HCTD)

Autori
Marchand, A.P. ; Wang, Y. ; Alihodžić, Sulejman ; Barton, D.H.R.

Izvornik
Tetrahedron (0040-4020) 53 (1997), 4; 1257-1264

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
cage compounds; oxidation; saturated-hydrocarbons; molecular-oxygen; gif system; mechanism

Sažetak
Gif-type reactions have been used to perform direct oxidative functionalization of the title compound (HCTD, 1). Thus, GoAgg(III) and GoAgg(IV) promoted oxidations of 1 afford 1-(2'-pyridyl)heptacyclo[6.6.0.0(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 heptacyclo[6.6.0.0(2, 6).0(3, 13).0(4, 11).0(5, 9).0(10, 14)]tetradecan-7-one (HCTD-3-one, 3) and 1-(4'-pyridyl)HCTD (4) in low isolated yield. Finally, oxidation of 1 performed by using an Fe-II-t-BuOOH system afforded several products, including hexacyclo[6.6.0, 0(2, 6).0(3, 13).0(4, 11).0(5, 9)]tetradecane-10, 14-dione (6) and 14-hydroxyhexacyclo[6.6.0, 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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