HYDROXYLATION OF POLYCYCLIC ALKANES WITH MOLECULAR-OXYGEN CATALYZED BY N-HYDROXYPHTHALIMIDE (NHPI) COMBINED WITH TRANSITION-METAL SALTS

Authors
ISHII Y KATO S IWAHAMA T SAKAGUCHI S
Citation
Y. Ishii et al., HYDROXYLATION OF POLYCYCLIC ALKANES WITH MOLECULAR-OXYGEN CATALYZED BY N-HYDROXYPHTHALIMIDE (NHPI) COMBINED WITH TRANSITION-METAL SALTS, Tetrahedron letters, 37(28), 1996, pp. 4993-4996
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
28
Year of publication
1996
Pages
4993 - 4996
Database
ISI
SICI code
0040-4039(1996)37:28<4993:HOPAWM>2.0.ZU;2-9
Abstract
Adamantanes were successfully converted into the corresponding mono- a nd dihydroxy adamantanes with molecular oxygen in the presence of N-hy droxyphthalimide (NHPI) combined with cobalt salts under mild conditio ns. For example, exposure of adamantane under oxygen atmosphere in the presence of NHPI (10 mol%) and Co(acac)(2) (0.5 mol%) in acetic acid at 75 degrees C for 6 h afforded adamantan-1-ol (43 %) and adamantane- 1,3-diol (40 %) along with adamantan-2-one (8 %) in 93 % conversion. S imilarly, 1,3-dimethyladamantane produced 3,5-dimethyladamantan-1-ol ( 47 %) and 5,7-dimethyladamantane-1,3-diol (37 %). Copyright (C) 1996 E lsevier Science Ltd