4
04
V. D. Filimonov et al.
PAPER
Iodination of Arenes by Reagents 1b,c in the Presence of
Ag SO ; General Procedure
(10) Yusubov, M. S.; Tveryakova, E. N.; Krasnokutskaya, E. A.;
Perederina, I. A.; Zhdankin, V. V. Synth. Commun. 2007, 37,
1259.
2
4
Ag SO (1.9 g, 6 mmol) was dissolved in a 93% H SO (15 mL).
2
4
2
4
Small portions of the reagent 1b or 1c (6 mmol) were added to the
solution at 5–7 °C. The precipitated AgCl was filtered off. An aro-
matic substrate (3 mmol) was added to the resulting dark-brown so-
lution of the iodinating reagent. The reaction was allowed to
proceed with stirring for the time indicated in Table 1. Isolation of
iodine derivatives was carried out under the above mentioned pro-
cedure for the iodination of arenes by the reagents 1b,c.
(11) (a) For example, the NMR spectra for 4-iodoanisole given in
6
the paper differ sharply from those published in other
1
1b
13
papers (see ref. ) – there are only six C signals instead of
five, and carbons are missing at appropriate shifts to be next
1
3
to iodine and OCH group (d = 82.5 and 159.4). In the
C
3
6
NMR spectrum of 3-iodo-4-methoxybenzyl alcohol there
are no Caryl–I and Caryl–OCH (d = 89 and 156) signals as
3
well. The reported melting point (mp 142–144 °C) of 3-
6
iodo-4-methoxybenzyl alcohol indicated in the paper is
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totally different from those previously published (mp
1
1c
11d
8
4 °C, mp 81–82 °C ), and similar inconsistence is
(
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5
b
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1
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Synthesis 2008, No. 3, 401–404 © Thieme Stuttgart · New York