Progressive Direct Iodination of Sterically Hindered Alkyl Substituted Benzenes

Stojan  Stavber; Petra  Kralj; Marko  Zupan

doi:10.1055/s-2002-33339

PAPER

Progressive Direct Iodination of Sterically Hindered Alkyl Substituted
Benzenes

Stojan Stavber*, Petra Kralj, Marko Zupan
Laboratory for Organic and Bioorganic Chemistry, ‘Joef Stefan’ Institute and Department of Chemistry, University of Ljubljana, Jamova 39, 1000 Ljubljana, Slovenia
Fax: +386(61)4773811; e-Mail: stojan.stavber@ijs.si;

Abstract

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Abstract

Benzene derivatives bearing at least one bulky alkyl group (i-Pr or t-Bu) were selectively and effectively iodinated using elemental iodine activated by 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor^TM, F-TEDA-BF₄). Iodine atoms were progressively introduced at the most electron-rich and sterically less hindered position on the benzene ring. Not more than three iodine atoms could be progressively bonded to a target molecule bearing a i-Pr or t-Bu group.

Key words

iodination - sterically hindered benzenes - Selectfluor^TM (F-TEDA-BF₄)

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