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Acknowledgement
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We thank Ankara University Research Fund (Grant
No. 2005-07-05-096) for financial support.
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1
3
pressure of nitrogen, using freshly distilled THF over
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tions. Alkyl halides 1a–i and allylic compounds 3a–c were
obtained commercially and purified using literature pro-
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tion. CuCN was purified according to the published
3
4
. (a) Organozinc Reagents. A Practical Approach; Knochel,
P., Ed.; Oxford University Press: Oxford, 1999; (b) Erdik,
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1
4
procedure. A three-necked flame-dried flask equipped
with a reflux condenser, two dropping funnels and a
magnetic stirrer was charged with Mg (24 mmol, 0.580 g)
and CuCN (2 mmol, 0.180 g) at room temperature.
Solutions of an alkyl bromide (20 mmol) in THF (5 mL)
and an allylic halide (10 mmol) in THF (5 mL) were added
separately to the stirred mixture at room temperature. The
reaction was started by adding a few drops of alkyl
bromide. The addition rate of the solutions was main-
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À1
1991, 251–253; (g) Goering, H. L.; Underiner, T. L. J.
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stirred at room temperature for 1.5 h. The aqueous layer
was extracted with ether. The combined organic solutions
were concentrated by rotary evaporation and subjected to
silica gel column chromatography with petroleum ether as
eluent to give a colourless liquid as a mixture of a- and c-
5
1
products. The a:c ratio was determined by 500 MHz H
1
24–130; (b) Tominoga, S.; Oi, Y.; Kato, T.; An, K. D.;
NMR analysis and also by GC analysis on a DB-1 glass
1
Okamoto, S. Tetrahedron Lett. 2004, 45, 5585–5588; (c)
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capillary column packed with dimethylpolysiloxane.
H
NMR spectroscopic data for the coupling products of a
selected reaction (1f–3a coupling, Table 2, entry 6):
(CDCl ), d: Compound 4: 0.90 (t, 3H, J = 7 Hz), 1.29
3
(m, 12H), 1.64 (d, 3H, J = 7 Hz), 1.86 (q, 2H, J = 7 Hz),
5.40 (m, 2H). Compound 5: 0.88 (t, 3H, J = 7 Hz), 0.98 (d,
3H, J = 7 Hz), 1.29 (m, 12H), 2.10 (m, 1H) 4.90 (dd, 1H,
J = 8 Hz, 2 Hz), 4.95 (dd, 1H, J = 17 Hz, 2 Hz), 5.70 (ddd,
1H, J = 17 Hz, 8 Hz, 6 Hz).
2
895–2903, and references cited therein.
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6
1
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2