W.R. Dolbier Jr. et al. / Journal of Fluorine Chemistry 127 (2006) 1302–1310
1307
solvent in most cases provided the products in essentially pure
form without the need for additional purification.
3.2.9. 4-Chloro-1-pentafluorosulfanylpent-2-ene (9)
1H NMR, d 5.93 (m, 2H), 4.55 (m, 1H), 4.27 (m, 2H), 1.63
(m, 3H); 19F NMR, d 85.3 (q, 1F), 57.1 (d, 4F).
3.2.1. 2-Chloro-1-pentafluorosulfanyloctane (1) [16]
1H NMR, d 0.90 (m, 3H), 1.35 (br s, 6H), 1.45 (m, 1H), 1.56
(m, 1H), 1.75 (m, 1H), 1.90 (m, 1H), 3.95 (m, 2H, CH2SF5),
4.35 (m, 1H, CHCl); 19F NMR, dA 82.9 (p, 1F), dB 65.7 (d,
J
37.7, 56.1 (p, J = 4.5 Hz), 77.2 (p, J = 12.1 Hz).
3.2.10. 2-Chloro-3-pentafluorosulfanylprop-1-ene (10)
[13]
1H NMR, d 5.69 (m, 1H), 5.65 (m, 1H), 4.40 (q, J = 5.5 Hz,
2H); 19F NMR, d 79.8 (q, 1F), 65.0 (d, 4F).
AB = 146 Hz, 4F); 13C NMR, d 14.2, 22.8, 26.2, 28.7, 31.8,
3.2.11. 1-Chloro-2-pentafluorosulfanylethyl acetate (11)
[14]
1H NMR, d 2.10 (s, 3H), 4.10 (m, 1H), 4.24 (m, 1H, CHSF5),
6.89 (dm, J = 10 Hz, 1H, CHCl); 19F NMR, dA 80.3 (p, 1F), dB
66.0 (d, JAB = 147 Hz, 4F); 13C NMR, d 20.7, 73.6 (m,
J = 14.6 Hz), 77.0 (m, J = 5.5 Hz), 167.8.
3.2.2. 2-Chloro-1-pentafluorosulfanylhexane (2) [16,26]
1H NMR, d 0.86 (t, J = 7 Hz, 3H), 1.2–1.5 (m, 4H), 1.68 (m,
1H), 1.85 (m, 1H), 3.87 (m, 2H, CH2SF5), 4.27 (m, 1H, CHCl);
19F NMR, dA 82.9 (p, 1F), dB 65.7 (d, JAB = 143 Hz, 4F); 13C
NMR, d 14.0, 22.1, 28.3, 37.4, 56.5 (p, J = 5.1 Hz), 77.5 (p,
J = 13.1 Hz).
3.2.12. Ethyl 4-chloro-5-pentafluorosulfanylpentanoate
(12)
3.2.3. 2-Chloro-3,3-dimethyl-1-pentafluorosulfanylbutane
(3) [16]
1H NMR, d 0.99 (s, 9H), 3.88 (m, 2H, CH2SF5), 4.11 (m, 1H,
CHCl); 19F NMR, dA 83.9 (p, 1F), dB 65.4 (d, JAB = 148 Hz,
4F); 13C NMR, d 26.5, 37.2, 65.8 (p, J = 4.1 Hz), 76.0 (p,
13.9 Hz).
1H NMR, d 4.39 (m, J = 3.3 Hz, 1H), 4.09 (q, J = 7.1 Hz,
2H), 3.90 (m, J = 6.4 Hz, 1H), 2.50 (m, 2H), 2.29 (m, 1H), 1.90
(m, 1H), 1.20 (t, J = 7.1 Hz, 3H); 19F NMR, dA 82.4 (q, 1F), dB
66.1 (d, JAB = 147 Hz, 4F); 13C NMR, d 14.75, 31.31, 33.17,
55.57 (m), 61.46, 77.23 (m), 172.71.
3.2.4. 2-Chloro-2-ethyl-1-pentafluorosulfanylbutane (4)
[16]
1H NMR, d 1.10 (t, J = 7.3 Hz, 6H), 2.02 (q, J = 7.3 Hz, 4H),
4.02 (pd, J = 8.8 and 2.9 Hz, 2H, CH2SF5); 19F NMR, dA 83.9
(p, 1F), dB 69.6 (d, JAB = 147 Hz, 4f); 13C NMR, d 8.7, 33.5,
75.9 (m), 76.9(m).
3.2.13. 5-Chloro-6-pentafluorosulfanylhexan-2-one (13)
1H NMR, d 4.42 (m, 1H), 3.96 (m, 2H), 2.73 (t, J = 7.8 Hz,
2H), 2.31 (m, 1H), 2.19 (s, 3H), 1.88 (m, 1H); 19F NMR, dA 82.4
(p, 1F), 65.9 (d, JAB = 146 Hz, 4F); 13C NMR, d 30.34, 31.60,
39.99, 55.63 (m), 77.23 (m), 207.11; Anal. Calcd for
C6H10OSF5: C, 27.65; H, 3.87. Found: C, 27.32; H, 3.70.
3.2.5. 4-Chloro-3-pentafluorosulfanylhexane (5) [16]
1H NMR, d 0.96 (m, 6H), 1.4–2.2 (overlapping m, 8H), 4.18
(m, 1H, CHSF5), 4.51 (br d, J = 10.2 Hz, 1H, CHCl); 19F NMR,
dA 85.8 (p, 1F), dB 59.5 (d, JAB = 144 Hz, 4F); 13C, d 13.4, 14.0,
20.5, 21.6, 31.0, 36.0, 60.9 (m, J = 4.9 Hz), 92.4 (m,
J = 16.7 Hz).
3.2.14. 9-Chloro-10-pentafluorosulfanyldecan-1-ol (14)
[26]
1H NMR, 4.30 (m,1H), 3.93 (m, 4H), 3.36 (t, J = 6 Hz, OH),
1.2–2.0 (m, 14H); 19F NMR, dA 88.9 (p, 1F), dB 65.7 (d,
JAB = 147 Hz, 4F); 13C NMR, d 26.08, 26.10, 28.80, 28,86,
29.36, 29.64, 29.91, 55.95 (m), 62.37, 77.10 (m).
3.2.6. 1-Chloro-2-pentafluorosulfanylcyclohexane (6)
[12,16]
1H NMR, d 1.4–2.2 (overlapping m, 8H), 4.04 (m, 1H,
CHSF5), 4.49 (m, 1H, CHCl); 19F NMR, dA 85.2 (p, 1F), dB 57.2
(d, JAB = 141 Hz, 4F); 13C NMR, d 21.4, 23.1, 27.0, 34.0, 57.0
(p, J = 3.5 Hz), 88.6 (m, J = 8.0 Hz).
3.2.15. 9-Chloro-10-pentafluorosulfanyldecyl acetate (15)
[26]
1H NMR, d 4.24 (m, 1H), 3.94 (t, J = 8 Hz, 2H), 3.86 (m,
2H), 1.92 (s, 3H), 1.80 (m, 1H), 1.65 (m, 1H), 1.16–1.58 (m,
12H); 19F NMR, dA 82.76 (p, 1F), dB 65.45 (d, JAB = 147 Hz,
4F); 13C NMR, d 26.12, 26.20, 28.86, 28.94, 29.36, 29.50,
31.89, 37.72, 56.11 (m), 64.72, 77.24 (m), 171.0.
3.2.7. 1-Chloro-1-(4-methylphenyl)-2-
pentafluorosulfanylethane (7) [16]
3.2.16. 1-Bromo-9-chloro-10-pentafluorosulfanyldecane
(16)
1H NMR, d 4.34 (m, 1H), 3.96 (m, 2H), 3.39 (t, J = 7 Hz,
2H), 1.90–1.20 (m, 14H); 19F NMR, dA 82.85 (p, 1F), dB 65.70
(d, JAB = 146 Hz, 4F); 13C NMR, d 28.40, 28.91, 28.96, 29.48,
31.92, 33.08, 34.21, 37.77, 56.12 (m), 77.23 (m).
1H NMR, d 2.25 (s, 3H), 4.18 (m, 2H, CH2SF5), 5.24 (t,
J = 6.6 Hz, 1H, CHCl) 7.10 and 7.18 (AB, JAB = 8.1 Hz, 4H);
19F NMR, dA 82.2 (p, 1F), dB 66.1 (d, JAB = 145 Hz, 4F); 13C
NMR, d 21.4, 56.5 (m, J = 5 Hz), 77.5 (m, J = 13.0 Hz), 127.0,
130.0, 135.7, 139.6.
3.2.8. 5-Chloro-6-pentafluorosulfanylhex-1-ene (8)
1H NMR, d 5.75 (m, 1H), 5.11 (m, 2H), 4.39 (m, 1H), 3.95
(m, 2H), 2.5–1.7 (m, 4H); 19F NMR, d 82.77 (p, 1F), 65.91 (d,
4F).
3.2.17. Methyl 3-chloro-4-pentafluorosulfanylbutanoate
(17)
1H NMR, d 4.75 (m, 1H), 4.08 (m, 2H), 4.34 (s, 3H), 3.0 (dd,
J = 16.6, 5.5 Hz, 1H), 2.85 (dd, J = 16.3, 7.7 Hz, 1H); 19F