J Surfact Deterg
3
C6F13), 31.96 (t, CH2CH2C6F13, JC–F = 22.13 Hz), 35.43
(s, CH2SC2H4C6F13), 61.60 (s, OCH2CH2OH), 70.57 (s,
SCH2CHOHCH2), 72.79 (m, 2 9 (CH2OCH2)), 74.53 (s,
CHOHCH2O), 3.67 (m, 20H, OCH2(CH2OCH2)4CH2),
4.01 (m, H, SCH2CHOH) ppm. 13C-{1H} NMR (CDCl3/
TMS): d = 23.63 (s, CH2CH2C6F13), 29.83 (t, CH2CH2
CH2CHOHCH2O), 110.72–117.72 (m, C6F13) ppm. 19F
C6F13, JC–F = 21.73 Hz), 35.13 (s, CH2SC2H4C6F13),
3
3
NMR (CDCl3/CFCl3): d = -82.33 (t, 3F, CF3, JFF
=
61.54 (s, CH2CH2OH), 70.09 (s, SCH2CHOHCH2), 72.23
(m, CH2(CH2OCH2)4), 74.02 (s, CHOHCH2O), 109.13–
117.47 (m, C6F13) ppm. 19F RMN (CDCl3/CFCl3): d =
9.72 Hz), -115.60 (m, 2F, CF2a), -123.22 (m, 2F, CF2b),
-124.56 (m, 2F, CF2d), -124.71 (m, 2F, CF2c), -127.82
(m, 2F, CF2x) ppm. Anal. Calc. for C15H19F13O4S: C,
33.22; H, 3.53. Found: C, 33.36; H, 3.49.
3
-82.76 (t, 3F, CF3, JFF = 8.56 Hz), -115.58 (m, 2F,
CF2a), -123.46 (m, 2F, CF2b), -124.54 (m, 2F, CF2d),
-124.69 (m, 2F, CF2c), -127.95 (m, 2F, CF2x) ppm. Anal.
Calc. for C21H31F13O7S: C, 37.39; H, 4.63. Found: C,
37.44; H, 4.13.
a-(2-F-hexylethyl)thiomethyl Tetraethylene Glycol
(5c)
1H NMR (CDCl3/TMS): d = 2.35 (m, 2H, SCH2CH2C6
F13), 2.69 (m, 2H, CH2SC2H4C6F13), 2.70–2.86 (m, 2H,
SCH2CH2C6F13), 3.41 (m, 2H, 2 9 OH), 3.69–3.73 (m,
14H, (CH2OCH2)3CH2), 4.05 (m, H, SCH2CHOH) ppm.
13C-{1H} NMR (CDCl3/TMS): d = 23.52 (s, CH2CH2C6
F13), 31.96 (t, CH2CH2C6F13, 3JC–F = 22.16 Hz), 35.43 (s,
CH2SC2H4C6F13), 61.60 (s, CH2CH2OH), 70.57 (s, SCH2
CHOH), 72.05 (s, (OCH2CH2)2OCH2), 74.53 (m, CHOH-
CH2O), 110.72–117.72 (m, C6F13) ppm. 19F RMN (CDCl3/
CFCl3): d = -82.33 (m, 3F, CF3), -115.60 (m, 2F, CF2a),
-123.22 (m, 2F, CF2b), -124.56 (m, 2F, CF2d), -124.71
(m, 2F, CF2c), -127.82 (m, 2F, CF2x) ppm. Anal. Calc. for
C17H23F13O5S: C, 34.82; H, 3.95. Found: C, 34.79; H,
4.02.
a-(2-F-octylethyl)thiomethyl Diethylene Glycol (5a0)
1H NMR (CDCl3/TMS): d = 2.31–2.54 (m, 2H,
SCH2CH2C8F17), 2.77 (m, 2H, CH2SC2H4C8F17), 2.97 (m,
2H, SCH2CH2C8F17), 3.50–3.65 (m, 2H, CHOHCH2O),
3.67 (m, 4H, OCH2CH2OH ? 2 9 OH), 3.73 (m, 2H,
OCH2CH2OH), 4.00 (m, H, SCH2CHOH) ppm. 13C-{1H}
NMR (CDCl3/TMS): d = 23.49 (s, CH2CH2C8F17), 32.25
3
(t, CH2CH2C8F17, JC–F = 21.96 Hz), 35.42 (s, CH2
SC2H4C8F17), 61.24 (m, OCH2CH2OH), 70.59 (s, SCH2
CHOHCH2), 72.68 (s, OCH2CH2OH), 74.23 (s, CH2CHO
HCH2O), 128.86 (m, C8F17) ppm. 19F NMR (CDCl3/
3
CFCl3): d = -82.82 (t, 3F, CF3, JFF = 9.76 Hz),
-115.28 (m, 2F, CF2a), -122.20 (m, 2F, CF2b?d),
-123.75 (m, 2F, CF2e), -124.36 (m, 2F, CF2n), -127.71
(m, 2F, CF2x) ppm. Anal. Calc. for C15H15F17O3S: C,
30.11; H, 2.53. Found: C, 30.19; H, 2.88.
a-(2-F-hexylethyl)thiomethyl Pentaethylene Glycol
(5d)
1H NMR (CDCl3/TMS): d = 2.30–2.50 (m, 2H,
SCH2CH2C6F13), 2.75 (m, 2H, CH2SC2H4C6F13), 2.83 (m,
2H, SCH2CH2C6F13), 3.52 (m, 2H, OCH2CHOHCH2O),
3.69 (m, 18H, CH2(CH2OCH2)3CH2 ? 2 9 OH), 4.05 (m,
H, SCH2CHOH) ppm. 13C-{1H} NMR (CDCl3/TMS):
d = 23.51 (s, CH2CH2C6F13), 29.52 (t, CH2CH2C6F13,
3JC–F = 21.21 Hz), 35.98 (s, CH2SC2H4C6F13), 65.43
(s, OCH2CH2OH), 70.57 (s, SCH2CHOH), 72.68 (m,
OCH2(CH2 OCH2)3), 74.99 (s, CH2CHOHCH2O),
108.94–120.12 (m, C6F13) ppm. 19F RMN (CDCl3/CFCl3):
d = -82.52 (t, 3F, CF3, 3JFF = 9.76 Hz), -115.69 (m, 2F,
CF2a), -123.34 (m, 2F, CF2b), -124.36 (m, 2F, CF2c),
-124.82 (m, 2F, CF2d), -127.70 (m, 2F, CF2x) ppm. Anal.
Calc. for C19H27F13O6S: C, 34.82; H, 3.95. Found: C,
34.79; H, 3.98.
a-(2-F-octylethyl)thiomethyl Triethylene Glycol (5b0)
1H NMR (CDCl3/TMS): d = 2.35 (m, 2H, SCH2
CH2C8F17), 2.69 (m, 2H, CH2SC2H4C8F17), 2.73–2.86 (m,
2H, SCH2CH2C8F17), 3.51 (m, 2H, 2 9 OH), 3.67 (m,
10H, CH2(OCH2CH2)2), 4.00 (m, H, SCH2CHOH) ppm.
13C-{1H} NMR (CDCl3/TMS): d = 23.17 (s, CH2CH2
3
C8F17), 32.13 (t, CH2CH2C8F17, JC–F = 21.96 Hz), 35.54
(s, CH2SC2H4C8F17), 61.71 (s, OCH2CH2OH), 70.57 (s,
SCH2CHOH), 72.68 (m, OCH2CH2OCH2), 74.25 (s,
CHOHCH2O), 112.14–122.23 (m, C8F17) ppm. 19F RMN
(CDCl3/CFCl3): d = -82.14 (t, 3F, CF3, 3JFF = 9.23 Hz),
-113.89 (m, 2F, CF2a), -121.96 (m, 6F, CF2b?d),
-123.01 (m, 2F, CF2e), -123.48 (m, 2F, CF2n), -126.98
(m, 2F, CF2x) ppm. Anal. Calc. for C17H19F17O4S: C,
31.79; H, 2.98. Found: C, 31.53; H, 3.01.
a-(2-F-hexylethyl)thiomethyl Hexaethylene Glycol
(5e)
a-(2-F-octylethyl)thiomethyl Tetraethylene Glycol
(5c0)
1H NMR (CDCl3/TMS): d = 2.30–2.46 (m, 2H,
SCH2CH2C6F13), 2.78 (m, 2H, CH2SC2H4C6F13), 2.85 (m,
2H, SCH2CH2C6F13), 3.40 (m, 2H, 2 9 OH), 3.56 (m, 2H,
1H NMR (CDCl3/TMS): d = 2.28–2.56 (m, 2H,
CH2CH2C8F17), 2.87 (m, 2H, CH2SC2H4C8F17), 3.04 (m,
123