D.W. Kim et al. / Tetrahedron 64 (2008) 4209e4214
4213
1
3
þ
C NMR (100 MHz, CDCl ) d 29.0, 37.1, 63.0, 66.8, 106.5,
3
C H F (M ) 188.1001, found 188.1001. Registry no. pro-
13 13
1
18.6, 123.8, 126.4, 126.7, 127.6, 129.0, 129.5, 134.4, 156.3;
þ
þ
vided by the author: 561009-56-1.
MS (EI) m/z 280 (M ); HRMS (EI) m/z calcd for C H O S
(M ) 280.0769, found 280.0770. Registry no. provided by the
author: 463934-08-9.
1
4 16 4
4
.4.2. 1-(2-Fluoroethyl)naphthalene
1
H NMR (600 MHz, CDCl ) d 3.49 (dt, J¼13.7, 6.9 Hz, 2H),
3
4
.75 (dt, J¼47.4, 6.9 Hz, 2H), 7.37e7.54 (m, 4H), 7.75e8.02
4
4
.3. Starting material for Table 2
13
(
8
1
m, 3H); C NMR (150 MHz, CDCl ) d 33.8 (d, J¼20.1 Hz),
3
3.5 (d, J¼168.0 Hz), 123.3, 125.5, 125.6, 126.2, 127.1, 127.5,
.3.1. 2-(3-Bromopropoxy)naphthalene
28.9, 132.0, 132.8 (d, J¼8.5 Hz), 133.8; MS (EI) m/z 174
1
H NMR (400 MHz, CDCl ) d 2.36e2.43 (m, 2H), 3.67 (t,
3
þ
(M ), 141 (100). Anal. Calcd: C, 82.73; H, 6.36. Found: C,
J¼6.6 Hz, 2H), 4.23 (t, J¼5.6 Hz, 2H), 7.14e7.17 (m, 2H),
8
2
2.63; H, 6.34. Registry no. provided by the author: 693785-
5-0.
1
.34e7.49 (m, 2H), 7.74e7.80 (m, 3H); C NMR (100 MHz,
3
7
CDCl ) d 30.1, 32.2, 65.2, 106.6, 118.8, 123.7, 126.4, 126.7,
3
þ
1
27.6, 128.9, 129.4, 134.4, 156.5; MS (EI) m/z 264 (M ), 266
þ
79
þ
(M ); HRMS (EI) m/z calcd for C H O Br (M ) 264.0150,
found 264.0151. Registry no. provided by the author: 3245-62-3.
4.4.3. 1-Vinylnaphthalene
Compound 7 (14 mg, 9%) as a by-product in the above re-
1
action was obtained as a colorless oil. H NMR (600 MHz,
1
3 13
CDCl ) d 5.47 (dd, J¼10.7, 1.7 Hz, 1H), 5.79 (dd, J¼17.5,
4
.3.2. 2-(3-Chloropropyl)naphthalene
3
1
8
.8 Hz, 1H), 7.43e7.52 (m, 4H), 7.61e7.62 (m, 1H), 7.77e
H NMR (400 MHz, CDCl ) d 2.16e2.23 (m, 2H), 2.97 (t,
3
1
.85 (m, 2H), 8.10e8.12 (m, 1H); C NMR (150 MHz,
3
7
CDCl ) d 117.1, 123.6, 123.7, 125.6, 125.7, 126.0, 128.1,
J¼7.4 Hz, 2H), 3.58 (t, J¼6.4 Hz, 2H), 7.35e7.37 (m, 1H),
1
3
7
.44e7.51 (m, 2H), 7.67 (s, 1H), 7.80e7.85 (m, 3H);
NMR (100 MHz, CDCl ) d 32.8, 33.8, 44.2, 125.3, 126.0,
C
3
þ
þ
1
1
1
28.5, 131.1, 133.6, 134.4, 135.6; MS (EI) m/z 154 (M ),
53 (100), 76; HRMS (EI) m/z calcd for C H (M )
3
1
26.7, 127.1, 127.4, 127.6, 128.1, 132.1, 133.5, 138.1; MS
þ
12 10
54.0783, found 154.0784. Registry no. provided by the
(EI) m/z 204 (M ), 141 (100), 115. HRMS (EI) m/z calcd
for C H Cl (M ) 204.0706, found 204.0702. Registry no.
þ
author: 826e74-4.
1
3 13
provided by the author: 27650-58-4.
4
.4.4. 2-Fluoromethylnaphthalene
1
4
.3.3. 1-(2-Methanesulfonylethyl)naphthalene
H NMR (200 MHz, CDCl ) d 5.57 (d, J¼47.6 Hz, 2H),
3
1
1
7.50e7.58 (m, 3H), 7.87e7.93 (m, 4H); C NMR (50 MHz,
3
H NMR (400 MHz, CDCl ) d 2.79 (s, 3H), 3.55 (t,
3
J¼7.2 Hz, 2H), 4.54 (t, J¼7.2 Hz, 2H), 7.40e7.59 (m, 4H),
CDCl ) d 84.7 (d, J¼165.8 Hz), 124.9, 125.0, 126.4, 126.4,
3
1
.79e8.03 (m, 3H); C NMR (100 MHz, CDCl ) d 32.7,
3
7
3
1
3
126.6, 126.7, 127.7, 127.8, 128.0, 128.1, 128.4, 133.1,
133.4, 133.5, 133.8; MS (EI) m/z 160 (M ). Anal. Calcd: C,
þ
7.2, 69.6, 123.0, 125.5, 125.8, 126.5, 127.5, 127.9, 128.9,
þ
31.6, 132.0, 133.8; MS (EI) m/z 250 (M ); HRMS (EI) m/z
82.48; H, 5.66. Found: C, 82.45; H, 5.26. Registry no.
provided by the author: 55831-11-3.
þ
calcd for C H O S (M ) 250.0664, found 250.0700. Regis-
1
3
14
3
try no. provided by the author: 119744-43-3.
4
.4.5. 1-(3-Fluoropropyl)-4-nitroimidazole
4
.3.4. 1-(3-p-Toluenesulfonyloxypropyl)-4-nitroimidazole
1
1
H NMR (400 MHz, CDCl ) d 2.14e2.27 (m, 2H), 4.22 (t,
3
H NMR (400 MHz, CDCl ) d 2.17e2.23 (m, 2H), 2.46 (s,
3
J¼7.0 Hz, 2H), 4.45 (dt, J¼46.8, 5.4 Hz, 2H), 7.47 (d,
3
7
H), 4.02 (t, J¼5.6 Hz, 2H), 4.16 (t, J¼6.8 Hz, 2H),
1
3
1
3
J¼1.2 Hz, 1H), 7.83 (d, J¼1.6 Hz, 1H); C NMR (100 MHz,
.36e7.38 (m, 3H), 7.66 (s, 1H), 7.76 (d, J¼8.4 Hz, 2H);
C
CDCl ) d 31.1 (d, J¼19.7 Hz), 44.3 (d, J¼4.5 Hz), 79.7 (d,
3
NMR (100 MHz, CDCl ) d 21.4, 29.7, 44.1, 66.0, 119.5,
3
1
þ
J¼166.0 Hz), 119.5, 136.2, 148.0; MS (EI) m/z 173 (M ,
27.5, 129.9, 131.7, 136.1, 145.4, 147.7; MS (EI) m/z 325
þ
þ
100), 127, 61. HRMS (EI) m/z calcd for C
H
8
FN
O
(M )
6
3
2
(
(
M ), 324, 91 (100). HRMS (EI) m/z calcd for C H N O S
M ) 325.0732, found 325.0717. Registry no. provided by the
1
3 15 3 5
þ
173.0601, found 173.0633. Registry no. provided by the author:
75831-82-0.
6
author: 675831-81-9.
4
.4. Fluorination product for Table 2
4.5. Polymer-supported ionic liquids (PSIL)
4
.4.1. 2-(3-Fluoropropyl)naphthalene
4.5.1. Polystyrene-supported 1-n-hexyl-3-methylimid-
1
H NMR (400 MHz, CDCl ) d 2.07e2.20 (m, 2H), 2.95 (t,
3
azolium tetrafluoroborate, PS[hmim][BF ]
4
1
3
0
0
J¼7.6 Hz, 2H), 4.52 (dt, J¼47.6, 6.0 Hz, 2H), 7.37e7.39 (m,
C NMR (solid state) d 27e31 (C2 eC5 ), 37 (NeCH ),
3
1
3
0
1
H), 7.45e7.53 (m, 2H), 7.68 (s, 1H), 7.84e7.87 (m, 3H);
C
41 (aliphatic polystyrene skeleton), 50 (C1 ), 72 (O-benzylic
0
NMR (100 MHz, CDCl ) d 31.4 (d, J¼5.4 Hz), 31.9 (d,
carbon and C6 ), 128 (C4, C5, aromatic polystyrene skeleton),
3
1
9
J¼19.7 Hz), 83.0 (d, J¼163.7 Hz), 125.3, 126.0, 126.6,
137 (C2), 146 (aromatic polystyrene skeleton); F NMR
(solid state) d ꢁ148. Anal. N, 6.2 (2.2 mmol ionic liquid
portion/g); Cl, 0.1.
1
1
27.2, 127.4, 127.6, 128.0, 132.0, 133.6, 138.5; MS (EI) m/z
88 (M ), 141 (100), 115. HRMS (EI) m/z calcd for
þ