ACCEPTED MANUSCRIPT
1
regioisomers in 1:1.25 ratio: Colorless oil; 35.5 mg, Yield: 76 %. H NMR (400
MHz, CDCl ) of 3h: δ 7.57 – 7.54 (m, 2H), 7.53 – 7.51 (m, 1H), 7.44 – 7.37 (m,
3
4
1
1
=
H), 4.50 (t,
J = 6.0 Hz, 1H), 4.38 (t, J = 5.8 Hz, 1H), 3.05 (t, J = 8.0 Hz, 2H),
13
.92 – 1.82 (m, 4H). C NMR (100 MHz, CDCl ) δ 133.9, 133.8, 133.5, 133.1,
3
28.4, 127.4, 126.9, 126.6, 126.3, 125.7, 83.6 (d,
J
= 165.1 Hz), 33.2, 29.5 (d, J
19
1
19.8 Hz), 25.1 (d,
J
= 5.0 Hz). F NMR (376 MHz, CDCl ) δ -218.54. H
3
NMR (400 MHz, CDCl ) of 3h’: δ 8.40 (d,
J
= 8.0 Hz, 1H), 7.83 (d,
H),7.78 – 7.76 (m, 1H), 7.73 – 7.71 (m, 3H), 7.50 – 7.45 (m, 1H), 4.48 (t,
.0 Hz, 1H), 4.36 (t, = 5.8 Hz, 1H), 3.00 (t, = 8.0 Hz, 2H), 1.82 – 1.72 (m,
H). C NMR (100 MHz, CDCl ) δ 134.0, 131.8, 128.6, 128.2, 127.7, 127.3,
J = 8.0 Hz,
3
1
6
4
1
2
3
J =
J
J
1
3
3
27.1, 126.4, 125.6, 125.1, 83.6 (d,
J
= 165.1 Hz), 33.9, 29.5 (d,
J = 19.8 Hz),
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5.1 (d,
J = 5.0 Hz). F NMR (376 MHz, CDCl ) δ -218.50; FTIR (film) 3441,
3
-1
054, 2961, 2867, 1926, 1589, 1501, 1384, 1268, 1038, 813, 790 cm ; HRMS
+
+
(
ESI) m/z calcd for C H FS [M+H] 235.0951, found 235.0953.
14 16
(4-fluorobutyl)(3-methoxyphenyl)sulfane(3i): Colorless oil; 33.4 mg, Yield:
1
7
1
8 %, H NMR (400 MHz, CDCl ) δ 7.20 (t,
J
= 8.0 Hz, 1H), 6.95 – 6.89 (m,
= 2.1 Hz, 1H), 6.76 – 6.69 (m, 1H), 4.52 (t, = 5.8 Hz, 1H), 4.40
= 5.6 Hz, 1H), 3.80 (s, 3H), 2.97 (t, = 7.0 Hz, 2H), 1.98 – 1.69 (m, 4H).
C NMR (100 MHz, CDCl ) δ 159.9, 137.7, 129.7, 121.2, 114.5, 111.6, 83.6 (d,
3
H), 6.87 (t,
J
J
(
t,
J
J
13
3
19
J
= 165.1 Hz), 55.3, 33.1, 29.4 (d,
J = 19.8 Hz), 25.0 (d, J = 4.8 Hz). F NMR
(
376 MHz, CDCl ) δ -218.66; FTIR (film) 3452, 2960, 1590, 1575, 1479, 1283,
3
-
1
+
+
1
2
248, 1041, 862, 771 cm ; HRMS (ESI) m/z calcd for C H FOS [M+H]
11 16
15.0900, found 215.0904.
1
(
3-fluoropropyl)(phenyl)sulfane(3j): Colorless oil; 25 mg, Yield: 74 %, H
NMR (400 MHz, CDCl ) δ 7.37 – 7.32 (m, 2H), 7.32 – 7.24 (m, 2H), 7.22 –
3
7
.14 (m, 1H), 4.61 (t,
J = 5.7 Hz, 1H), 4.49 (t, J = 5.7 Hz, 1H), 3.04 (t, J = 7.2
13
Hz, 2H), 2.09 – 1.91 (m, 2H). C NMR (100 MHz, CDCl ) δ 135.9, 129.4,
3
1
29.0, 126.2, 82.2 (d,
J
= 165.6 Hz), 30.1 (d,
J = 20.2 Hz), 29.4 (d, J = 4.7 Hz).
19
F NMR (376 MHz, CDCl ) δ -221.05; FTIR (film) 3432, 2969, 2923, 1630,
3
1
3