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Synthesis 2008(16): 2510-2512  
DOI: 10.1055/s-2008-1067205
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Fluorination of Adamantanes with Iodine Pentafluoride

Shoji Hara*, Motoshi Aoyama
Graduate School of Engineering, Hokkaido University, Sapporo 060-8628 Japan
Fax: +81(11)7066556; e-Mail: shara@eng.hokudai.ac.jp;
Further Information

Publication History

Received 14 April 2008
Publication Date:
24 July 2008 (online)

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Abstract

Direct fluorination of adamantanes was achieved by iodine pentafluoride and one or two fluorine atoms were introduced selectively on the tertiary carbons of adamantanes.

Key words

adamantane - direct fluorination - regioselectivity - hypervalent­ iodine - iodine pentafluoride

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8

More than one fluorine atom of IF5 is used and one equivalent of IF5 is not necessary for the fluorination.7a

9

Even at 75 ˚C, the difluorinated product of methyl adaman-tane-1-carboxylate or 1-(acetoxymethyl)adamantane was not obtained.