1370
Can. J. Chem. Vol. 82, 2004
2JHgem = 15.6 Hz, -CH2P), 7.30–7.50 (m, 5H, -Ph). 13C NMR
(DMSO-d6, 200 MHz) δ: 13.1, 16.9 (d, 1JCP = 46.7 Hz), 22.5
References
2
3
1
(d, JCP = 4.2 Hz), 23.3 (d, JCP = 15.5 Hz), 25.4 (d, JCP
=
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Benzyltributylphosphonium chloride (3ab) (40, 41)
White crystals, mp 163 to 164 °C. 1H NMR (CDCl3,
3
300 MHz) δ: 0.92 (t, 9H, JHH = 6.59 Hz, 3 × -CH3), 1.43–
1.48 (m, 12H, 3 × -CH2CH2), 2.38–2.48 (m, 6H, 3 × -CH2P),
4.31 (d, 2H, 2JHgem = 15.38 Hz, -CH2P), 7.33–7.39 (m, 3H, -Ph),
1
7.45–7.49 (m, 2H, -Ph). H NMR (DMSO-d6, 200 MHz) δ:
3
0.90 (t, 9H, JHH = 6.75 Hz, 3 × -CH3), 1.30–1.50 (m, 12H,
3 × -CH2CH2), 2.10–2.30 (m, 6H, 3 × -CH2P), 3.90 (d, 2H,
2JHgem = 15.6 Hz, -CH2P), 7.30–7.50 (m, 5H, -Ph). 13C NMR
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2
1
1
(d, JCP = 5 Hz), 23.5 (d, JCP = 15.7 Hz), 25.5 (d, JCP
=
80 Hz), 128.0, 129.0, 129.5, 130.0
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Hexyltriphenylphosphonium bromide (5ba) (42, 43)
1
mp 195–198 °C. H NMR (CDCl3, 300 MHz) δ: 082 (t,
3
3H, J = 6.78 Hz, -CH3), 1.19–1.28 (m, 4H, 2 × -CH2),
1.57–1.69 (m, 4H, 2 × -CH2), 3.80 (m, 2H, -CH2P), 7.68–
7.89 (m, 15H, 3 × -Ph). Insoluble in diethyl ether or toluene
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Hexyltriphenylphosphonium chloride (5bb)
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mp 209 to 210 °C. 1H NMR (CDCl3, 300 MHz) δ: 0.82 (t,
3
3H, J = 6.87 Hz, -CH3), 1.18–1.28 (m, 4H, 2 × -CH2),
1.57–1.68 (m, 4H, 2 × -CH2), 3.92 (m, 2H, -CH2P), 7.67–
7.92 (m, 15H, 3 × –Ph). 13C NMR (CDCl3, 200 MHz) δ:
2
1
13.0, 21.2, 21.5 (d, JCP = 3.7 Hz), 21.5 (d, JCP = 49.6 Hz),
3
1
29.1 (d, JCP = 15.3 Hz), 30.2, 117.3 (d, JCP = 82.5 Hz),
3
2
129.6 (d, JCP = 12.3 Hz), 132.6 (d, JCP = 9.8 Hz), 134.2.
Insoluble in diethyl ether or toluene at their respective boil-
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Hexyltributylphosphonium bromide (5aa)
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–CH3), 1.29–1.35 (m, 4H, 2 × –CH2), 1.47–1.60 (m, 16H,
8 × –CH2), 2.40–2.53 (m, 8H, 4 ×-CH2P). The product be-
haves like an ionic liquid and becomes solid upon freezing
(–18 °C); insoluble in diethyl ether at room temperature.
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Hexyltributylphosphonium chloride (5ab)
3
1H NMR (CDCl3, 250 MHz) δ: 0.90 (t, 3H, J = 6.96 Hz,
3
-CH3), 1.00 (t, 9H, J = 6.79 Hz, 3 × -CH3), 1.20–1.40 (m,
4H, 2 × -CH2), 1.40–1.70 (m, 16H, 8 × -CH2), 2.30–2.60 (m,
8H, -CH2P). 13C NMR (CDCl3, 250 MHz) δ: 13.2, 13.7, 18.7
1
1
2
(d, JCP = 47.4 Hz), 18.9 (d, JCP = 47.0 Hz), 21.5 (d, JCP
=
=
3
3
5 Hz), 22.1, 23.6, 23.7 (d, JCP = 15.2 Hz), 30.2 (d, JCP
14.7 Hz), 30.8. The product behaves like an ionic liquid and
becomes solid upon freezing (–18 °C); insoluble in diethyl
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Acknowledgments
This work was supported by Slovak grant agency VEGA
grant No. 1/7348/20 and was carried out under the auspices
of COST D10, project No. 00014/98.
© 2004 NRC Canada