Efficient Oxidation of Adamantanes by Sodium Nitrite with Molecular Oxygen in Trifluoroacetic Acid

Osamu Onomura; Yutaka Yamamoto; Noriaki Moriyama; Fumiaki Iwasaki; Yoshihiro Matsumura

doi:10.1055/s-2006-950422

LETTER

Efficient Oxidation of Adamantanes by Sodium Nitrite with Molecular Oxygen in Trifluoroacetic Acid

Osamu Onomura^a, Yutaka Yamamoto^a, Noriaki Moriyama^a, Fumiaki Iwasaki^b, Yoshihiro Matsumura*^a
^a Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyomachi, Nagasaki 852-8521, Japan
Fax: +81(95)8192476; e-Mail: matumura@net.nagasaki-u.ac.jp;
^b Tsukuba Research Lab, Tokuyama Co. Ltd., 40 Wadai, Tsukuba 300-4247, Japan

Abstract

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Abstract

Oxidation of adamantanes by oxygen was effectively achieved by use of sodium nitrite as a catalyst in trifluoroacetic acid (TFA) to give 1-adamantyl trifluoroacetates, from which adamantanols were obtained in good yields. A catalytic amount of sodium nitrite was essential and TFA was the best solvent among solvents examined for this oxidation.

Key words

alcohols - hydrocarbons - oxidations - oxygen - radical reactions

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