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Jo200522w Si 002
Jo200522w Si 002
Jo200522w Si 002
Department of Chemistry and Applied Bioscience, Swiss Federal Institute of Technology, ETH Zürich, CH-8093 Zürich, Switzerland
E-Mail: atogni@ethz.ch
SUPPORTING INFORMATION
1
H NMR of dipropyl phosphonate (2b)……………………………………………………………………...........................................….S2
1
H NMR of diisopropyl phosphonate (2c)……………………………………………………………………............................................S3
1
H NMR of diisobutyl phosphonate (2e)……………………………………………………………………................…………………..S4
1
H NMR of dineopentyl phosphonate (2f)…………………………………………………………………….......................................….S5
1
H NMR of dicyclohexyl phosphonate (2g)…………………………………………………………………….....................................….S6
1
H NMR of bis(2-chloroethyl) phosphonate (2h)…………………………………………………………………................................….S7
1
H NMR of bis(3-chloropropyl) phosphonate (2i)…………………………………………………………………..............................….S8
1
H, 13C, 31P NMR of bis(4-chlorobutyl) phosphonate (2j)…………………………………………………………..………................….S9
1
H NMR of bis(2-methoxyethyl) phosphonate (2k)…………………………………………………………………..................………...S12
1
H NMR of O,O-diethyl S-hydrogen phosphorothioate (3a)…………………………………………………………...………………….S13
1
H, 13C, 31P NMR of O,O-dipropyl S-hydrogen phosphorothioate (3b)……………………………………………………………………S14
1
H NMR of O,O-diisopropyl S-hydrogen phosphorothioate (3c)………………………………………………………………………….S17
1
H NMR of O,O-dibutyl S-hydrogen phosphorothioate (3d)………………………………………………………………………………S18
1
H NMR of O,O-diisobutyl S-hydrogen phosphorothioate (3e)……………………………………………………………………………S19
1
H, 13C, 31P NMR of O,O-dineopentyl S-hydrogen phosphorothioate (3f)…………………………………………………………………S20
1
H, 13C, 31P NMR of O,O-dicyclohexyl S-hydrogen phosphorothioate (3g)………………………………………………………..………S23
1
H, 13C, 31P NMR of O,O-bis(2-chloroethyl) S-hydrogen phosphorothioate (3h)………………………………………………………….S26
1
H, 13C, 31P NMR of O,O-bis(3-chloropropyl) S-hydrogen phosphorothioate (3i)…………………………………………………………S29
1
H, 13C, 31P NMR of O,O-bis(4-chlorobutyl) S-hydrogen phosphorothioate (3j)………………………………………………….……….S32
1
1
H, 13C, 31P NMR of O,O-bis(2-methoxyethyl) S-hydrogen phosphorothioate (3k)……………………………………………….……….S35
1
H, 13C NMR of O,O-diethyl S-trifluoromethyl phosphorothioate (4a)………………………………………………………….....………S38
1
H, 13C NMR of O,O-diisopropyl S-trifluoromethyl phosphorothioate (4c)………………………………………………………..………S40
1
H, 13C, 31P, 19F NMR of O,O-dicyclohexyl S-trifluoromethyl phosphorothioate (4g)……………………………………………..………S42
2
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H
P
O
O
ppm 11
Cl
Cl
10
300 MHz 1H NMR in CDCl3
bis(4-chlorobutyl) phosphonate (2j)
9
8
7.979
0.5
7
6
5.658
0.496
5
4.148
4.131
4.123
4.111
4
4.01
4.103
4.084
3.596
3.576
4.04
3.557
3
1.949
1.938
1.931
1.928
1.921
1.915
2 1.908
1.887
8.12
1.877
1.867
1.847
1.839
1.825
1
1.824
1.806
0
-1
10
bis(4-chlorobutyl) phosphonate (2j)
75.5 MHz 13C NMR in CDCl3
O
64.941
64.864
44.268
28.639
27.792
27.707
P
H O
O
Cl
Cl
11
bis(4-chlorobutyl) phosphonate (2j)
121.5 MHz 31P NMR in CDCl3
O
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7.813
H O
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Cl
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12
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