6
4
S.-T. Fu et al. / Journal of Fluorine Chemistry 147 (2013) 56–64
ꢀ
1
(
376.50 MHz, CDCl
3
):
d
ꢀ80.7 (s, 3F), ꢀ112.1 (s, 2F), ꢀ121.3 (s, 2F),
1215, 1151, 743, 713 cm . Anal. calcd. for C12
10 2
H F17NO S: C,
ꢀ
126.0 (s, 2F). FTIR (film): 2936, 1458, 1392, 1241, 1208, 1140,
25.96; H, 1.82; N, 2.52. Found: C, 25.91; H, 1.88; N, 2.61.
ꢀ
1
7
3
43, 724 cm . Anal. calcd. for C10 NO S: C, 28.92; H, 3.40; N,
H
14
F
9
4
.37. Found: C, 28.98; H, 3.48; N, 3.42.
4.3.20. N,N-di(2-methoxyethyl)-perfluorooctanesulfonamide (5d, n-
8 2 2(1O2)
C F17SO N )
1
4
C
.3.13. N,N-dimethyl-perfluorohexanesulfonamide (4a, n-
Colorless liquid, yield 71%, bp 134 8C (5 mmHg). H NMR
(400.13 MHz, CDCl
(376.50 MHz, CDCl
1
9
6
F
13SO
2
N
11
)
3
):
):
d
d
3.37 (s, 2 ꢆ 3H), 3.66 (m, 4 ꢆ 2H). F NMR
ꢀ80.4 (s, 3F), ꢀ112.7 (s, 2F), ꢀ120.2 (s, 2F),
1
white solid, yield 90%. H NMR (400.13 MHz, CDCl
ꢆ 3H). F NMR (376.50 MHz, CDCl
3
):
d
3.12 (s,
3
19
2
2
3
):
d
ꢀ80.7 (s, 3F), ꢀ111.6 (s,
ꢀ121.7 (t, 3 ꢆ 2F), ꢀ122.7 (s, 2F), ꢀ126.1 (s, 2F). FTIR (film): 2937,
ꢀ1
F), ꢀ120.6 (s, 2F), ꢀ121.8 (s, 2F), ꢀ122.7 (s, 2F), ꢀ126.1 (s, 2F).
1459, 1392, 1243, 1214, 1153, 781, 706 cm . Anal. calcd. for
14 14 4
C H F17NO S: C, 27.33; H, 2.29; N, 2.28. Found: C, 27.41; H, 2.38;
ꢀ
1
FTIR (KBr): 2966, 1461, 1374, 1244, 1207, 1147, 794, 674 cm
.
Anal. calcd. for C
8
H
6
F
13NO
2
S: C, 22.49; H, 1.42; N, 3.28. Found: C,
N, 2.31.
2
2.58; H, 1.48; N, 3.32.
Acknowledgements
4.3.14. N-ethyl-N-methyl-perfluorohexanesulfonamide (4b, n-
C
6
F
13SO
2
N
12
)
We thank the National Natural Science Foundation of China (no.
1
White solid, yield 91%. H NMR (400.13 MHz, CDCl
3
):
J = 7.2 Hz, 3H), 3.07 (s, 3H), 3.48 (m, 2H). F NMR (376.50 MHz,
CDCl ):
ꢀ80.8 (s, 3F), ꢀ112.3 (s, 2F), ꢀ120.6 (s, 2F), ꢀ121.9 (s, 2F),
122.8 (s, 2F), ꢀ126.2 (s, 2F). FTIR (KBr): 2987, 1466, 1376, 1243,
d 1.28 (t,
5
1172083), and the Independent Innovation Research Fund,
Huazhong University of Science and Technology (no.
011QN110) for the financial support.
19
3
d
2
ꢀ
ꢀ
1
1
209, 1148, 795, 670 cm . Anal. calcd. for C
9 8 2
H F13NO S: C, 24.50;
References
H, 1.83; N, 3.17. Found: C, 24.58; H, 1.88; N, 3.22.
[
1] R.J. Cremlyn, M.J. Frearson, S. Graham, Phosphorus, Sulfur, and Silicon 107 (1995)
05–217.
[2] K. Fujii, K. Hatano, K. Tsutsumiuchi, A. Ooka, Y. Nakamoto, H. Umeyama, JP patent
000136179 A2, 2000.
[3] H.J. Lehmler, Chemosphere 58 (2005) 1471–1496.
[4] H.J. Lehmler, V.V.V.N.S. Rama Rao, D. Nauduri, J.D. Vargo, S. Parkin, J. Fluorine
Chem. 128 (2007) 595–607.
2
4
.3.15. N,N-diethyl-perfluorohexanesulfonamide (4c, n-C
Colorless liquid, yield 93%, bp 114 8C (10 mmHg). H NMR
400.13 MHz, CDCl ):
1.27 (t, J = 7.2 Hz, 2 ꢆ 3H), 3.49 (m, 2 ꢆ 2H).
F NMR (376.50 MHz, CDCl ):
ꢀ80.8 (s, 3F), ꢀ112.7 (s, 2F),
120.4 (s, 2F), ꢀ121.8 (s, 2F), ꢀ122.7 (s, 2F), ꢀ126.1 (s, 2F). FTIR
6 2 22
F13SO N )
1
2
(
1
3
d
9
3
d
ꢀ
[
[
5] G.L. Li, L.Q. Zheng, J.X. Xiao, J. Fluorine Chem. 130 (2009) 674–681.
6] Z. Benfodda, F. Guillen, B. Romestand, A. Dahmani, H. Blancou, Eur. J. Med. Chem.
45 (2010) 1225–1229.
ꢀ1
(
film): 2988, 1469, 1392, 1241, 1212, 1122, 741, 707 cm . Anal.
calcd. for C10 S: C, 26.38; H, 2.21; N, 3.08. Found: C,
6.48; H, 2.28; N, 3.01.
10 2
H F13NO
[7] C.P. Zhang, Z.L. Wang, Q.Y. Chen, C.T. Zhang, Y.C. Gu, J.C. Xiao, J. Fluorine Chem. 131
2
(2010) 761–766.
[8] M. Schmidt, P. Sartori, N. Ignat’ev, Eur. Patent 1088814, 2001.
4
.3.16. N,N-di(2-methoxyethyl)-perfluorohexanesulfonamide (4d, n-
[9] W.L. Xu, R.H. Tao, Y.Q. Wang, X.Q. Xu, Z.F. Si, X.R. Chen, P.X. Ding, X. Li, Y.M. Wang,
CN patent 101747245, 2008.
[10] Q.Y. Chen, Z.M. Qiu, J. Fluorine Chem. 31 (1986) 301–317.
C
6 2 2(1O2)
F13SO N )
1
Colorless liquid, yield 77%, bp 113 8C (5 mmHg). H NMR
[
11] T.J. Huang, Z.X. Dong, J.M. Shreeve, Inorg. Chem. 26 (1987) 2604–2606.
[12] A.R. Katritzky, T.L. Davis, G.W. Rewcastle, G.O. Rubel, M.T. Pike, Langmuir 4 (1988)
32–735.
13] I.M. Lyapkalo, H.U. Reissig, A. Sch a¨ fer, A. Wagner, Helv. Chim. Acta 85 (2002)
206–4215.
1
9
(
(
400.13 MHz, CDCl
376.50 MHz, CDCl
3
):
):
d
d
3.37 (s, 2 ꢆ 3H), 3.68 (m, 4 ꢆ 2H). F NMR
ꢀ80.8 (s, 3F), ꢀ112.0 (s, 2F), ꢀ120.3 (s, 2F),
7
3
[
ꢀ
121.8 (s, 2F), ꢀ122.7 (s, 2F), ꢀ126.1 (s, 2F). FTIR (film): 2936,
4
ꢀ1
1
459, 1392, 1242, 1208, 1150, 741, 707 cm . Anal. calcd. for
S: C, 27.97; H, 2.74; N, 2.72. Found: C, 28.04; H, 2.78;
[14] A.W. Li, X. Bin, S.Z. Zhu, J. Fluorine Chem. 69 (1994) 257–259.
[15] G.R. Leader, Anal. Chem. 45 (1973) 1700–1706.
C
12 14 4
H F13NO
[
16] J. Graton, M. Berthelot, C. Laurence, J. Chem. Soc. Perkin Trans. 2 (2001) 2130–
135.
17] P. Sartori, N. Ignat’ev, S. Datsenko, J. Fluorine Chem. 75 (1995) 157–161.
N, 2.65.
2
[
4
.3.17. N,N-dimethyl-perfluorooctanesulfonamide (5a, n-
[18] L.P. Oznobikhina, N.N. Chipanina, T.N. Aksamentova, B.A. Shainyan, Russ. J. Gen.
Chem. 79 (2009) 1674–1682.
C
8 2 11
F17SO N )
[
19] S. Benefice-Malouet, H. Blancou, R. Teissedre, A. Commeyras, J. Fluorine Chem. 31
1986) 319–332.
[20] D.C. Dearden, Sci. Total Environ. 109/110 (1991) 59–68.
1
White solid, yield 89%. H NMR (400.13 MHz, CDCl
3
):
d 3.13 (s,
(
19
2
2
ꢆ 3H). F NMR (376.50 MHz, CDCl
3
): d
ꢀ80.8 (s, 3F), ꢀ111.7 (s,
[21] R.J.C. Brown, R.F.C. Brown, J. Chem. Educ. 77 (2000) 724–731.
[22] Z.B. Zhou, H. Matsumoto, K. Tatsumi, Chem. Eur. J. 12 (2006) 2196–2212.
[23] S. Malik, Synth. Commun. 38 (2008) 3074–3081.
F), ꢀ120.6 (s, 2F), ꢀ121.8 (t, 3 ꢆ 2F), ꢀ122.8 (s, 2F), ꢀ126.2 (s, 2F).
ꢀ1
FTIR (KBr): 2967, 1461, 1374, 1240, 1212, 1152, 752, 718 cm
.
Anal. calcd. for C10
H
6
F
17NO
2
S: C, 22.78; H, 1.15; N, 2.66. Found: C,
[24] L.J. Sacco, J. Am. Chem. Soc. 76 (1954) 303–305.
[
25] M. Morita, Y. Asai, N. Yoshimoto, M. Ishikawa, J. Chem. Soc. Faraday Trans. 94
1998) 3451–3456.
26] J. Barthel, M. Utz, K. Gross, H.J. Gores, J. Solut. Chem. 24 (1995) 1109–1123.
2
2.86; H, 1.28; N, 2.55.
(
[
4
.3.18. N-ethyl-N-methyl-perfluorooctanesulfonamide (5b, n-
[27] K. Naoi, E. Iwama, N. Ogihara, Y. Nakamura, H. Segawa, Y. Ino, J. Electrochem.
Chem. 156 (2009) A272–A276.
[28] C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, third ed., VCH,
New York, 2003.
[29] Y. Marcus, Pure Appl. Chem. 57 (1985) 1103–1208.
[30] J.F. Coetzee, T.H. Chang, Pure Appl. Chem. 58 (1986) 1535–1540.
C
8 2 12
F17SO N )
1
White solid, yield 90%. H NMR (400.13 MHz, CDCl
3
):
J = 7.2 Hz, 3H), 3.08 (s, 3H), 3.49 (m, 2H). F NMR (376.50 MHz,
CDCl ):
ꢆ 2F), ꢀ122.8 (s, 2F), ꢀ126.2 (s, 2F). FTIR (KBr): 2968, 1461, 1375,
d 1.28 (t,
19
3
d
ꢀ80.8 (s, 3F), ꢀ112.2 (s, 2F), ꢀ120.5 (s, 2F), ꢀ121.8 (t,
[31] K. Xu, M.S. Ding, S.S. Zhang, J.L. Allen, T.R. Jow, J. Electrochem. Chem. 150 (2003)
A161–A169.
3
1
2
ꢀ1
239, 1213, 1151, 752, 649 cm . Anal. calcd. for C11
8 2
H F17NO S: C,
[32] V. Gutmann, Angew. Chem. Int. Ed. 9 (1970) 843–860.
4.41; H, 1.49; N, 2.59. Found: C, 24.36; H, 1.48; N, 2.65.
[33] K. Dimroth, C. Reichardt, T. Siepmann, F. Bohlmann, Liebigs Ann. Chem. 661
1963) 1–37.
(
[
[
34] C. Reichardt, Chem. Rev. 94 (1994) 2319–2358.
35] M.J. Muldoon, C.M. Gordon, I.R. Dunkin, J. Chem. Soc. Perkin Trans. 2 (2001) 433–
435.
4
8 2 22
.3.19. N,N-diethyl-perfluorooctanesulfonamide (5c, n-C F17SO N )
1
White solid, yield 92%. H NMR (400.13 MHz, CDCl
3
):
d
1.27 (t,
):
ꢀ80.7 (s, 3F), ꢀ112.7 (s, 2F), ꢀ120.3 (s, 2F), ꢀ121.7 (t, 3 ꢆ 2F),
122.7 (s, 2F), ꢀ126.1 (s, 2F). FTIR (KBr): 2966, 1460, 1390, 1239,
19
[36] M.J. Kamlet, J.L. Abboud, R.W. Taft, J. Am. Chem. Soc. 99 (1977) 6027–6038.
J = 7.2 Hz, 2 ꢆ 3H), 3.50 (m, 2 ꢆ 2H). F NMR (376.50 MHz, CDCl
3
[
[
37] M.J. Kamlet, R.W. Taft, J. Am. Chem. Soc. 98 (1976) 377–383.
38] R.W. Taft, M.J. Kamlet, J. Am. Chem. Soc. 98 (1976) 2886–2894.
d
ꢀ
[39] S.N. Baker, G.A. Baker, F.V. Bright, Green Chem. 4 (2002) 165–169.