7
General procedure was followed with a reaction time of 2 h to
provide 2t in 90% isolated yield. Colourless liquid, 1H NMR (400
MHz, CDCl3) δ 3.98-3.75 (m, 1H), 1.65-1.54 (m, 2H), 1.54-1.40
(m, 1H), 1.38-1.20 (m, 5H), 0.93-0.80 (m, 3H), 0.15 (s, 9H). 13C
2.42-2.25 (m, 1H), 0.98 (d, J = 6.7 Hz, 3H), 0.71 (d, J = 6.8 Hz,
ACCEPTED MANUSCRIPT
3H), 0.22 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 139.3, 127.8,
1
2
127.7, 126.2 (q, J(C, F)= 288.7 Hz), 126.2, 83.5 (q, J(C, F) =
26.7 Hz), 35.8, 17.5, 17.4, 1.8. 19F NMR (376 MHz, CDCl3) δ -
69.6. IR (KBr): 3730, 3657, 3063, 2960, 2929, 2859, 1756, 1602,
1497, 1471, 1448, 1369, 1256, 1218, 1163, 1090, 1040, 1001,
935, 881, 844, 756, 723, 700, 662, 631, 542, 449 cm−1. MS (EI,
m/z) 290.1 (M+), 220.8 (M+-CF3). Anal. Calcd for C14H21F3OSi:
C, 57.90; H, 7.29. Found: C, 57.91; H, 7.21.
1
NMR (101 MHz, CDCl3) δ 125.2 (q, J(C, F)= 282.3 Hz), 71.1
2
(q, J(C, F) = 30.7 Hz), 31.5, 30.4, 24.7, 22.5, 13.9, -0.1. 19F
3
NMR (376 MHz, CDCl3) δ -79.1 (d, J(F, H) = 6.5 Hz). IR
(KBr): 3800, 3741, 3555, 2957, 2866, 2673, 1870, 1734, 1461,
1398, 1374, 1284, 1256, 1169, 1150, 1102, 1019, 966, 875, 846,
755, 690, 618, 585, 544, 500, 450 cm−1. MS (EI, m/z) 172.8 (M+-
CF3). Anal. Calcd for C10H21F3OSi: C, 49.56; H, 8.73. Found: C,
49.39; H, 8.64.
3.4.26. Trimethyl(2,2,2-trifluoro-1,1-diphenylethoxy)silane (4d)
General procedure was followed with a reaction time of 12 h
to provide 4d in 82% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 7.65-7.58 (m, 4H), 7.55-7.48 (m, 6H), 0.15
(s, 9H). 13C NMR (101 MHz, CDCl3) δ 140.9, 128.2, 128.1,
127.8, 125.2 (q, 1J(C, F)= 287.3 Hz), 81.9 (q, 2J(C, F) = 28.6 Hz),
1.2. 19F NMR (376 MHz, CDCl3) δ -72.6. The NMR data were in
agreement with reported results.15b
3.4.21. Trimethyl((1,1,1-trifluorooctan-2-yl)oxy)silane (2u)
General procedure was followed with a reaction time of 2 h to
1
provide 2u in 89% isolated yield. Colourless liquid, H NMR
(400 MHz, CDCl3) δ 3.98-3.76 (m, 1H), 1.65-1.54 (m, 2H), 1.49
(d, J = 6.3 Hz, 1H), 1.38-1.21 (m, 7H), 0.89 (t, J = 6.7 Hz, 3H),
1
0.15 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 125.3 (q, J(C, F)=
3.4.27. ((2-Cyclopropyl-1,1,1-trifluoropropan-2-
yl)oxy)trimethylsilane (4e)
2
282.3 Hz), 71.2 (q, J(C, F) = 30.7 Hz), 31.7, 30.5, 29.0, 25.1,
3
22.6, 14.0, -0.2. 19F NMR (376 MHz, CDCl3) δ -79.1 (t, J(F, H)
= 6.4 Hz). IR (KBr): 3803, 3743, 3651, 2956, 2864, 2671, 1870,
1698, 1545, 1460, 1387, 1260, 1165, 1055, 986, 850, 756, 691,
618, 586, 545, 506, 463 cm−1. MS (EI, m/z) 187.1 (M+-CF3).
Anal. Calcd for C11H23F3OSi: C, 51.53; H, 9.04. Found: C, 51.36;
H, 8.92.
General procedure was followed with a reaction time of 12 h
to provide 4e in 87% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 1.35 (s, 3H), 0.69-0.53 (m, 1H), 0.50-0.39
(m, 2H), 0.37-0.27 (m, 1H), 0.15 (s, 9H). 13C NMR (101 MHz,
CDCl3) δ 126.4 (q, J(C, F)= 286.5 Hz), 74.7 (q, J(C, F) = 28.1
Hz), 21.0, 15.8, 1.9, 0.7, -0.1. 19F NMR (376 MHz, CDCl3) δ -
82.0. IR (KBr): 2923, 2855, 2047, 1720, 1663, 1603, 1462, 1228,
971, 852, 738 cm−1. MS (EI, m/z) 156.8 (M+-CF3). Anal. Calcd
for C9H17F3OSi: C, 47.76; H, 7.57. Found: C, 47.39; H, 7.28.
1
2
3.4.22. (E)-Trimethyl((1,1,1-trifluoro-4-phenylbut-3-en-2-
yl)oxy)silane (2v)
General procedure was followed with a reaction time of 12 h
to provide 2v in 81% isolated yield. Colorless liquid, 1H NMR
(400 MHz, CDCl3) δ 7.35 (d, J = 7.5 Hz, 2H), 7.28 (t, J = 7.4 Hz,
2H), 7.22 (t, J = 7.2 Hz, 1H), 6.71 (d, J = 15.9 Hz, 1H), 6.20-6.08
(m, 1H), 4.74-4.33 (m, 1H), 0.15 (s, 9H). 13C NMR (101 MHz,
3.4.28. ((2-Cyclohexyl-1,1,1-trifluoropropan-2-
yl)oxy)trimethylsilane (4f)
General procedure was followed with a reaction time of 12 h
to provide 4f in 84% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 1.89-1.73 (m, 4H), 1.72-1.52 (m, 2H), 1.36-
0.93 (m, 8H), 0.15 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 126.7
1
CDCl3) δ 135.8, 135.0, 128.7, 128.4, 126.8, 124.3 (q, J(C, F)=
2
282.1 Hz), 122.4, 72.3 (q, J(C, F) = 32.5 Hz), -0.2. 19F NMR
(376 MHz, CDCl3) δ -78.5 (d, 3J(F, H) = 6.4 Hz). The NMR data
were in agreement with reported results.30
1
2
(q, J(C, F)= 287.9 Hz), 78.6 (q, J(C, F) = 26.8 Hz), 44.6, 27.4,
26.9, 26.6, 26.6, 26.4, 18.4, 2.0. 19F NMR (376 MHz, CDCl3) δ -
77.3. IR (KBr): 3645, 2925, 2856, 1733, 1665, 1592, 1457, 1372,
1294, 1256, 1164, 1097, 993, 848, 756, 682, 625, 526 cm−1. MS
(EI, m/z) 268.1 (M+), 198.8 (M+-CF3). Anal. Calcd for
C12H23F3OSi: C, 53.70; H, 8.64. Found: C, 53.91; H, 8.81.
3.4.23. Trimethyl((1,1,1-trifluoro-2-phenylpropan-2-yl)oxy)silane
(4a)
General procedure was followed with a reaction time of 12 h
to provide 4a in 91% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 7.65-7.49 (m, 2H), 7.49-7.23 (m, 3H), 1.82
(s, 3H), 0.15 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 140.1,
3.4.29. Trimethyl((1-(trifluoromethyl)cyclopentyl)oxy)silane (4g)
1
128.4, 128.0, 126.9, 125.4 (q, J(C, F)= 286.0 Hz), 77.0 (q, 2J(C,
General procedure was followed with a reaction time of 12 h
to provide 4g in 88% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 2.04-1.89 (m, 2H), 1.85-1.75 (m, 4H), 1.75-
1.60 (m, 2H), 0.15 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 126.5
F) = 32.4 Hz), 22.7, 1.9. 19F NMR (376 MHz, CDCl3) δ -81.6.
The NMR data were in agreement with reported results.15b
3.4.24. Trimethyl((1,1,1-trifluoro-2-phenylbutan-2-yl)oxy)silane
(4b)
1
2
(q, J(C, F)= 283.4 Hz), 84.2 (q, J(C, F) = 28.9 Hz), 35.8, 24.3,
1.6. 19F NMR (376 MHz, CDCl3) δ -80.2. The NMR data were in
agreement with reported results.31
General procedure was followed with a reaction time of 12 h
to provide 4b in 85% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 7.43 (d, J = 7.6 Hz, 2H), 7.34-7.20 (m, 3H),
2.14-2.06 (m, 1H), 2.06-1.95 (m, 1H), 0.65 (t, J = 7.4 Hz, 3H),
0.18 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 138.0, 128.0, 127.8,
126.8, 125.7 (q, 1J(C, F)= 287.2 Hz), 80.7 (q, 2J(C, F) = 27.9 Hz),
27.3, 6.9, 1.7. 19F NMR (376 MHz, CDCl3) δ -78.0. The NMR
data were in agreement with reported results.13c
3.4.30. Trimethyl((1-(trifluoromethyl)cyclohexyl)oxy)silane (4h)
General procedure was followed with a reaction time of 12 h
to provide 4h in 86% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 1.77 (d, J = 12.1 Hz, 2H), 1.67 (d, J = 13.0
Hz, 1H), 1.62-1.54 (m, 3H), 1.54-1.38 (m, 3H), 1.27-1.10 (m,
1H), 0.15 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 126.4 (q, 1J(C,
F)= 285.6 Hz), 75.5 (q, 2J(C, F) = 27.7 Hz), 30.9, 25.2, 20.6, 1.6.
19F NMR (376 MHz, CDCl3) δ -82.7. The NMR data were in
agreement with reported results.29
3.4.25. Trimethyl((1,1,1-trifluoro-3-methyl-2-phenylbutan-2-
yl)oxy)silane (4c)
General procedure was followed with a reaction time of 12 h
to provide 4c in 71% isolated yield. Colourless liquid, 1H NMR
(400 MHz, CDCl3) δ 7.46 (d, J = 7.6 Hz, 2H), 7.38-7.25 (m, 3H),
3.4.31. Trimethyl((1,1,1-trifluoro-2-methylhexan-2-yl)oxy)silane
(4i)