8664
J. Salabert et al. / Tetrahedron 67 (2011) 8659e8664
C24H17F17O2 requires C, 43.65; H, 2.59. IR (KBr, cmꢁ1): 2942, 2917,
2845, 1738, 1615, 1513, 1372, 1301, 1201, 1150, 1101, 1034, 941, 834,
823, 660, 565, 530. 1H NMR (CDCl3; 360 MHz) dH¼2.93 (1H, m), 3.16
(1H, m), 3.17 (3H, s), 3.81 (3H, s), 4.29 (1H, m), 6.85 (2H, d, J¼8.3),
7.12 (2H, d, J¼8.3), 7.22 (2H, d, J¼8.3), 7.44 (2H, d, J¼8.3). 13C NMR
(CDCl3; 90 MHz) dC¼44.5, 55.2, 56.5, 84.0, 113.8, 126.5 (t, J¼7), 126.7
(t, J¼24), 127.9, 129.7, 133.0, 143.0, 159.2. 19F{1H} NMR (CDCl3;
235 MHz) dF¼ꢁ81.3, ꢁ110.9, ꢁ121.7, ꢁ122.4, ꢁ123.2, ꢁ126.5.
4. (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72; (b) Gladysz, J. A. Science 1994,
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4.2.13. 1-(4-Methoxyphenyl)-2-(4-(perfluorooctyl)phenyl)ethanol
5c. The product was purified by column chromatography twice
using hexaneediethyl ether (95:5) as eluent and then using hex-
aneedichloromethane (8:2) as eluent affording 5c as a slightly
yellow solid (687 mg, 45% yield). Mp: 95e104 ꢀC. IR (KBr, cmꢁ1):
3407, 2921, 1614, 1517, 1372, 1300, 1203, 1150, 1103, 1048, 944, 835,
645. 1H NMR (CDCl3; 360 MHz) dH¼1.86 (1H, s), 3.02 (2H, m), 3.81
(3H, s), 4.88 (1H, m), 6.87 (2H, d, J¼8.6), 7.24 (2H, d, J¼9.2), 7.29 (2H,
d, J¼9.2), 7.50 (2H, d, J¼8.6). 13C NMR (CDCl3; 90 MHz) dC¼45.5,
55.3, 74.7, 113.9, 126.8 (t, J¼7), 127.1, 129.8, 135.6, 142.7, 159.3. 19F
{1H} NMR (CDCl3; 235 MHz) dF¼ꢁ81.2, ꢁ110.9, ꢁ122.3, ꢁ123.1,
ꢁ123.2, ꢁ126.5. HR-ESI (m/z): [calcd]: [MþNa]þ, 669.0698; [exptl.]:
[MþNa]þ, 669.0687.
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Financial support from the MICINN of Spain (Projects CTQ2007-
62771/BQU, CTQ2008-05409, CTQ2010-20387 and Consolider
Ingenio 2010 CSD2007-00006) and the DURSI-Generalitat de Cat-
alunya (2009SGR-1441 and 2009SGR-637) is acknowledged. We
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thank the Universitat Autonoma de Barcelona for the grant of J.S.
Supplementary data
Supplementary data containing 1H, 13C NMR, IR and HRMS
spectra of all new compounds described in this article will be
available. ESI-MS spectra corresponding to experiments described
in the text and selected TEM images of NPs observed during the
reactions are available. Supplementary data associated with this
article can be found, in the online version, at doi:10.1016/
€
VCH Weinheim: Weinheim, Germany, 2010; (f) Agrawal, D.; Schroder, D. Or-
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