W.R. Dolbier Jr., M. Okamoto / Journal of Fluorine Chemistry 179 (2015) 33–41
39
1-Benzimidazole-1-yl 1-fluorononane (3ak)
J = 3.5 Hz), 28.7, 29.1, 29.3, 31.8, 40.7 (d, J = 18.4 Hz), 95.7 (d,
J = 251 Hz).
1-Fluoro-1-iodononane, (3ap)
1H NMR,
d 0.88 (t, 3H, J = 6.6 Hz), 1.20–1.60 (m, 12 H), 2.15–2.46
1H NMR,
(m, 2H), 6.82 (dt, 1H, J = 49.8 Hz and 5.5 Hz); 19F NMR,
1F, J = 50.2 Hz and 19.7 Hz); 13C NMR,
14.0, 22.6, 26.7, 28.45, 29.1,
29.3, 31.8, 43.2 (d, J = 18.4 Hz), 75.6 (d, J = 253 Hz).
1-Benztriazole-1-yl 1-fluoropentane (3ba)
d
0.89 (t, 3H, J = 7.2 Hz), 1.28–1.52 (m, 12 H), 2.10–2.25
ꢀ136.1 (dt,
(m, 2H), 6.31 (dt, 1H, J = 51.7 Hz and 6.6 Hz), 7.34–8.12 (m, 5H); 19
F
d
NMR,
d
ꢀ136.2 (ddd, 1F, J = 51.4 Hz, 22.0 Hz and 10.2 Hz); 13C NMR,
d
13.9, 22.5, 24.4 (d, J = 4.6 Hz), 28.8, 28.9, 29.1, 31.6, 33.2 (d,
J = 25.2 Hz), 94.0 (d, J = 200 Hz), 110.3, 120.4, 123.2, 123.8, 132.65,
140.3, 143.7.
1-Benztriazole-1-yl 1-fluorononane (3al)
1H NMR,
d 0.93 (t, 3H, J = 7.1 Hz), 1.20–1.48 (m, 4H), 2.40–2.70
(m, 2H), 6.74 (dt, 1H, J = 50.8 Hz and 6.8 Hz), 7.35–8.12 (m, 4H); 19
F
1H NMR,
d 0.88 (t, 3H, J = 6.6 Hz), 1.20–1.60 (m, 12 H), 2.40–2.70
NMR,
d
ꢀ139.3 (ddd, 1F, J = 50.0 Hz, 21.6 Hz and 10.5 Hz); 13C NMR,
(m, 2H), 6.74 (dt, 1H, J = 50.4 Hz and 6.8 Hz), 7.41–8.13 (m, 4H); 19
F
d
13.6, 21.9, 26.3, 26.2, 32.3 (d, J = 24.1 Hz), 96.3 (d, J = 204 Hz),
NMR,
NMR,
d
ꢀ139.45 (ddd, 1F, J = 50.2 Hz, 21.8 Hz and 10.9 Hz); 13C
109.8, 120.1, 124.5, 128.2, 132.0, 146.3.
d
14.0, 22.55, 24.2, 28.65, 28.8, 29.1 (d, J = 12.5 Hz), 31.7, 32.7
1-Fluoropentyl acetate (3bb)
(d, J = 24.0 Hz), 96.5 (d, J = 204 Hz), 109.9, 120.3, 124.6, 128.2,
132.05, 146.5.
1-Fluorononane (3am)
1H NMR,
d 0.92 (t, 3H, J = 7.1 Hz), 1.30–1.43 (m, 4H), 1.75–1.82
(m, 2H), 2.13 (s, 3H), 6.31 (dt, 1H, J = 55.6 Hz and 5.3 Hz); 19F NMR,
d
ꢀ129.3 (ddd, 1F, J = 56.3 Hz, 19.6 Hz and 16.0 Hz); 13C NMR,
d
1H NMR,
d 0.88 (t, 3H, J = 7.2 Hz), 1.15–1.40 (m, 12 H), 1.68 (dt,
13.8, 20.8, 22.2, 25.0 (d, J = 4.6 Hz), 33.85 (d, J = 21.6 Hz), 103.2 (d,
J = 220 Hz), 169.2.
2H, J = 24.0 Hz and 6.6 Hz), 4.44 (dt, 1H, J = 47.4 Hz and 6.2 Hz); 19
F
NMR,
d
ꢀ218.5 (tt, 1F, J = 47.9 Hz and 24.1 Hz); 13C NMR,
d 14.1,
S-1-fluoropentyl O-ethyl dithiocarbonate (3bc)
22.7, 25.1, 25.2, 29.3, 29.5, 30.4 (d, J = 19.4 Hz), 31.9, 84.2 (d,
J = 163 Hz).
1-Chloro-1-fluorononane (3an)
1H NMR,
d 0.93 (t, 3H, J = 7.4 Hz), 1.30–1.55 (m, 8 H), 1.80–2.10
(m, 2H), 4.68 (q, 2H, J = 6.8 Hz), 6.45 (dt, 1H, J = 51.9 Hz and 6.5 Hz);
19F NMR,
d
ꢀ154.0 (dt, 1F, J = 52.0 Hz and 18.7 Hz); 13C NMR,
d 13.6,
1H NMR,
(m, 2H), 6.15 (dt, 1H, J = 51.0 Hz and 5.3 Hz); 19F NMR,
1F, J = 50.5 Hz and 17.5 Hz); 13C NMR,
14.1, 22.6, 24.2 (d,
d
0.89 (t, 3H, J = 7.2 Hz), 1.20–1.53(m, 12 H), 2.10–2.25
ꢀ130.7 (dt,
13.7, 22.1, 27.15 (d, J = 3.5 Hz), 33.45 (d, J = 21.6 Hz), 70.2, 100.1 (d,
J = 217 Hz), 210.1.
d
2-Phenyl 1-benztriazole-1-yl 1-fluoroethane (3ca)
d
J = 3.2 Hz), 28.8, 29.1, 29.3, 31.8, 39.3 (d, J = 19.4 Hz), 102.95 (d,
J = 240 Hz).
1-Bromo-1-fluorononane (3ao)
1H NMR,
6.5 Hz), 7.20–8.10 (m, 9 H); 19F NMR (282 MHz, CDCl3);
(ddd, 1F, J = 50.3 Hz, 21.2 Hz and 13.1 Hz); C NMR,
J = 25.2 Hz), 96.1 (d, J = 206 Hz), 109.65, 120.2, 124.6, 127.5, 128.3,
128.7, 129.4, 132.3, 133.5 (d, J = 5.7 Hz), 146.3.
d
3.84–3.95 (m, 2H), 6.87 (dt, 1H, J = 51.2 Hz and
ꢀ137.6
39.15 (d,
d
1H NMR,
(m, 2H), 6.45 (dt, 1H, J = 51.0 Hz and 5.3 Hz); 19F NMR,
1F, J = 51.0 Hz and 20.3 Hz); 13C NMR,
14.1, 22.6, 25.05 (d,
d
0.89 (t, 3H, J = 7.2 Hz), 1.20–1.53(m, 12 H), 2.10–2.25
ꢀ131.0 (dt,
d
d
d