Brindaban C. Ranu, R. Jana
FULL PAPER
3
, although iodination of a few sensitive substrates was carried out
with the temperature of the ultrasonic bath maintained at 20 °C
Table 1) and for chlorination the reaction mixture was heated at
0 °C in place of sonication, other experimental conditions being
kept identical.
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6
2289–2299; b) P. J. Garegg, B. Samuelsson, J. Chem. Soc., Per-
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1
All the products were properly characterized by IR, H NMR and
13
C NMR spectroscopic data. Many of these compounds are
known (references given in tables) and so are easily identified by
comparison with reported data. A few compounds for which spec-
troscopic data are not available are provided below in the order of
their entries in the Tables.
44, 3872–3881; f) A. K. Mandal, S. W. Mahajan, Tetrahedron
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1-Allyloxy-2-(bromomethyl)benzene (entry 7, X = Br, Table 1):
1
f
Colourless liquid; R =.60. H NMR: δ = 4.60 (s, 2 H), 4.62–4.67
(
1
2
m, 2 H), 5.28–5.32 (m, 1 H), 5.45–5.52 (m, 1 H), 6.03–6.15 (m,
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Green Chem.2002, 4, 357–360.
H), 6.85–6.95 (m, 2 H), 7.24–7.36 ppm (m, 2 H). 1 C NMR: δ =
3
9.4, 69.2, 112.6, 117.6 (2 C), 121.2, 130.4 (2 C), 131.2, 133.3 ppm.
–1
[5] S. Sunner, C. A. Wulff, J. Chem. Thermodyn.1974, 6, 287–292.
IR: ν˜ = 1608, 1512, 1251, 1031, 831 cm . C10H11BrO (226.00): C
5
nd
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2.89, H 4.88; found: C 52.72, H 4.82.
[
[
[
1
-Allyloxy-2-(iodomethyl)benzene (entry 7, X = I, Table 1): Yellow-
1
ish liquid; R
2
6
f
= 0.60. H NMR: δ = 4.53 (s, 2 H), 4.64–4.65 (m,
H), 5.31–5.35 (m, 1 H), 5.50–5.55 (m, 1 H), 6.07–6.18 (m, 1 H),
.85–6.95 (m, 2 H), 7.24–7.36 ppm (m, 2 H). 13C NMR: δ = 1.4
I), 68.7, 112.2, 117.3, 120.8, 127.7, 129.5, 130.2, 133.0,
[
10] D. D. Milena, M. Enrico, T. Elisabetta, J. Org. Chem.2000, 65,
(CH
2
2830–2833.
–
1
1
56.1 ppm. IR: ν˜ = 1603, 1510, 1460, 1250, 1030, 827 cm .
[11] J. Hellerbach, H. Hoffman, G. Zenetti, Ger. Offen.1974, 2, 347,
455 (Chem. Abst.1974, 81, 13568p).
10
C H
11IO (273.99): C 43.82, H 4.05; found: C 43.80, H 4.10.
[12] H. Safdar, A. Rahman, K. M. Khan, M. I. Chaudhary, G. M.
Maharvi, Z. Ullah, E. Bayer, Synth. Commun.2003, 33, 2531–
2
540.
Acknowledgments
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[
13] J. L. Kelley, M. P. Krochmal, J. A. Linn, E. W. McLean, F. E.
Soroko, J. Med. Chem.1988, 31, 606–612.
This investigation has enjoyed financial support from the CSIR,
New Delhi [Grant No. 01(1739)/02]. R. J. also thanks the CSIR for
his fellowship.
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81, 24624e).
[15] K. Kuehlein, H. Jensen, Justus Liebigs Ann. Chem.1974, 369–
02.
4
[
16] B. S. Orlek, P. G. Sammes, D. J. Weller, Tetrahedron1993, 49,
[
[
1] R. C. Larock, Comprehensive Organic Transformations, 2nd ed.,
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Received: August 23, 2004
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Eur. J. Org. Chem. 2005, 755–758