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Synthesis 2004(3): 441-445  
DOI: 10.1055/s-2004-815955
PAPER
© Georg Thieme Verlag Stuttgart · New York

Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant [1]

Piotr Lulinski, Anna Kryska, Maciej Sosnowski, Lech Skulski*
Chair and Laboratory of Organic Chemistry, Faculty of Pharmacy, Medical University, 1 Banacha Street, 02-097 Warsaw, Poland
Fax: +48(22)5720643; e-Mail: lskulski@farm.amwaw.edu.pl;
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Publikationsverlauf

Received 7 October 2003
Publikationsdatum:
06. Februar 2004 (online)

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Abstract

Three easy eco-friendly laboratory procedures are presented for the oxidative iodination of various activated and deactivated arenes with molecular iodine, in the presence of UHP (percarbamide), a stable, strongly H-bonded, solid urea-hydrogen peroxide adduct as the oxidant.

Key words

iodoarenes - arenes - halogenation - iodine - peroxides

1

These results were presented at the International Symposium on Frontiers in Molecular Science 2002, Qingdao, China, July 14-18, 2002.

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1

These results were presented at the International Symposium on Frontiers in Molecular Science 2002, Qingdao, China, July 14-18, 2002.

17

Varied quantities of conc. H2SO4 added to the reaction mixtures (established by us experimentally and given in the experimental section for each of the arenes iodinated) clearly depended on relative reactivities of the arenes investigated. The more deactivated the arene, the more conc. H2SO4 had to be added to catalyze better the oxidative iodination reaction. For more details see either Note 22 in Ref., [9] or (better) Ref., [4] pp 1334-1337.

19

The urea released from UHP is readily acetylated in hot Ac2O/AcOH/concd H2SO4 mixtures to give N-acetylurea ad-mixed with N,N′-diacetylurea. However, these side products are fully removable from the crude iodinated products during the workup and recrystallization.

20

The 1H NMR solution spectra run in this work to support the structures of the purified iodinated products are presented and discussed in: Lulinski P.; Ph.D. Thesis (in Polish); Faculty of Pharmacy, Medical University of Warsaw: Poland, 2002;