I. Wlassics, V. Tortelli / Journal of Fluorine Chemistry 129 (2008) 359–365
365
a
b
c
d
[
[
[
[
2] G. Houghhem (Ed.), Fluoropolymers, Academic Plenum Publishers, N.Y.,
1999.
ꢀ
ꢀ
–O– CF –O CF C(O CF )–2,2,4-trifluoro-5-trifluoro-
2 3
1
9
a
methoxy-1,3-dioxole (6): F NMR d À44.2 (s, 2F, CF ),
2
À1
3] R.D. Chambers, Fluorine in Organic Chemistry, Blackwell Publishing
Ltd, 2004 167–218.
d
b
À58.4 (s, 3F, O CF ), À145.5 (s, 1F, CF).FT-IR: 1851 cm
3
À1 À1 À1 À1
(
C C st), 1395 cm , 1304 cm , 1275 cm , 1239 cm ,
189 cm , 997 cm , 945 cm , 686 cm , 457 cm .MS
4] W. Navarrini, V. Tortelli, A. Russo, S. Corti, J. Fluorine Chem. 95 (1999)
27–39.
À1 À1 À1 À1 À1
1
5] W. Navarrini, V. Tortelli, P. Colaianna, J. Abusleme, US Patent 5,646,223,
CA 122 (1997) 187563.
(
(
m/z): 31 (25%), 47 (37%), 69 (100%), 116 (14%), 210
61%), 211 (0,7%).
[
[
[
6] M. Riva, Chem. Today 21 (2003) 310–311.
7] D.W. Smith, D.A. Babb, Macromolecules 29 (1996) 852–860.
8] J. Miki, H. Yoshimi, H. Aoyama European Patent 1,247,791; CA 135
(2000) 108913.
a
b
c
d
–O– CF –O CFH CCl(O CF )–5-chloro-2,2,4-trifluoro-4-
2
3
1
9
hydro-5-trifluoromethoxy-1,3-dioxolane. F NMR d À50.3
a
b
d
1
(
s, 2F, CF ), À137.6 (d, 1H, –O CFH), À56.1 (s, 3F CF ) H
2
3
b
[
9] T. Araki, T. Shimizu, T. Yamato, M. Kumegawa, Y. Yamamoto US Patent
NMR d 6.3 (m, 1H, CFH)MS (m/z): 29 (75%), 69 (75%), 96
60%), 132 (47%), 145 (100%), 161 (41%), 227 (0,95%).
5
,670,593; CA 124 (1997) 177249.
10] K. Takai, T. Kakiuchi, Y. Kataoka, K. Utimoto, J. Org. Chem. 59 (1994)
668–2670.
11] I.T. Horv a´ th, J. R a´ bai, Science 266 (1994) 72–75.
(
[
[
a
b
c
d
ꢀ
ꢀ
ꢀ
ꢀ
–O– CF –O CFCl CH(O CF )-4-chloro-2,2,4-trifluoro-5-
2 3
2
1
9
hydro-5-trifluoromethoxy-1,3-dioxolane: F NMR d À50.3
a
b
d
1
(
s, 2F, CF ), À62.2 (s, 1F, CFCl), À57.5 (s, 3F CF ); H
[12] E.G. Hope, A.M. Stuart, J. Fluorine Chem. 100 (1999) 75–83, and
references therein.
2
3
c
NMR d 5.1 (m, 1H, CH)
2,2-bis(4-(1-Bromo-tetrafluoroethoxy)phenyl)-1,1,13,3,3-
[
13] M. Cavezzini, F. Montanari, J. Fluorine Chem. 94 (1999) 183–193, and
references therein.
b
c
a
hexafluoropropane:(7), Br CF CF O–C H –C( CF ) C H -
2
2
6
4
3 2 6 4
[
14] S.J. Tavener, J.H. Clark, J. Fluorine Chem. 123 (2003) 31–36.
c
d
2
19
a
O CF CF Br [7]: F NMR d À62.5 (s, 6F, CF ), À68.3 (s,
2
3
[15] D.P. Curran, Z. Lee, Green Chem. 3 (2001) G3.
b
c
4
2,2-bis(4-(Trifluoroethenoxy)phenyl)-1,1,13,3,3-hexafluoro-
F, CF ), À85.2 (s, 4F, CF ).
[16] W.H. Saunders Jr., A.F. Cockeril, Mechanisms of Elimination Reactions,
Wiley, New York, 1973.
2
2
b
c
a
c
b
propane:(8), CF CFO–C H –C( CF ) C H –O CF CF2
[17] J.R. Gandler, Patai Supplement A: ‘‘The Chemistry of Double-
bonded Functional Groups Part 1’’ vol. 2, Wiley, New York, 1989,
2
6
4
a
3 2 6 4
1
9
b
[
7]: F NMR d À62.5 (s, 6F, CF ), À119.3 (q, 2F, CF ),
3
2
7
33–797.
b
c
À126.4 (q, 2F, CF ), À134.7 (q, 2F, CFO).
2
[18] R.A. More O’Ferrall, Patai ‘‘The Chemistry of the Carbon–Halogen Bond
Part 2’’, Wiley, New York, 1973, 609–675.
2,2-bis(4-(2-Hydrotetrafluoroethoxy)phenyl)-1,1,1,3,3,3-
a
b
c
[
19] H.F. Koch, Acc. Chem. Res. 17 (1984) 137–144.
hexafluoropropane:
c
H CF CF O–C H –C( CF ) C H –
2 2 6 4 3 2 6 4
d
19
a
[20] G.A. Olah, E.B. Baker, J.C. Evans, W.S. Tolgyesi, J.S. McIntyre, I.J.
Bastien, J. Am. Chem. Soc. 86 (1964) 1360–1373.
O CF CF H F NMR d À62.5 (s, 6F, CF ), À88.3 (s,
2
2
3
d
1
4
NMR d 7.6 (m, 8H, pH), 6.6 (t, 4H, –CF H).
F, –OCF CF H), À137.4 (d, 4F, J = 47 Hz, CF H). H
2
2
HF
2
[
21] I. Wlassics, V. Tortelli, European Patent 1,719,750; US Patent Appl.
0,252,966 (2006); CA 145 (2006) 471990.
2
a
b
Dimer of (7), [Br CF CF O–C H –C( CF ) C H –O C-
c
d
ꢀ
[22] I. Wlassics, V. Tortelli, European Patent 1,719,751; US Patent Appl.
,252,968 (2006); CA 145 (2006) 471244.
[23] W. Navarrini, S. Corti, J. Fluorine Chem. 125 (2004) 189.
2
2
6
4
3 2 6 4
e
19
a
0
F CF ] : F NMR d À62.5 (s, 12F, CF ), À68.3 (s, 4F,
2
2 2
3
b
c
d
CF ), À85.2 (s, 4F, CF ), À88.4 (s, 4F, CF ), À120.7 (s, 4
2
2
2
[
[
24] I. Wlassics, J. Fluorine Chem. 125 (2004) 1519–1528.
25] D.W. Smith, D.A. Babb, H.V. Shah, A. Hoeglund, R. Traiphol, D.
Perahia, H.W. Bone, C. Langhoff, M. Radler, J. Fluorine Chem. 104
(2001) 109.
e
F, CF ).
2
References
[
[
26] S.L. Mannat, M.T. Bowers, J. Am. Chem. Soc. 91 (1969) 4381.
27] W. Navarrini, L. Bragante, S. Fontana, V. Tortelli, A. Zedda, J. Fluorine
Chem. 71 (1995) 111.
[
1] D.S. Kemp, F. Vellaccio, Organic Chemistry, Worth Publishers, Inc., New
York, NY, 1980, 165–195.