SYNTHESIS AND STRUCTURE OF N-(DIAMINOMETHYLIDENE)- ...
1283
Bis(cyclohexylamino)-N-(trifluoromethylsul-
fonyl)methaniminium trifluoromethanesulfonate
(III). Trifluoromethanesulfonic acid, 0.10 ml (0.18 g,
1.2 mmol), was added under vigorous stirring to a so-
lution of 0.43 g (1.2 mmol) of compound II in 4 ml of
methylene chloride. The mixture was stirred for 3 h at
room temperature and evaporated under reduced pres-
sure, and the residue (colorless crystals) was dried un-
der reduced pressure. Yield 0.60 g (100%), mp 174°C.
IR spectrum, ν, cm–1: 3366, 3334, 3212, 3105, 2942,
2866, 1669, 1602, 1586, 1455, 1299, 1224, 1140, 1112,
no. 10-03-00110). The authors thank Dr. I.A. Ushakov
for recording the {1H}–13C NMR spectrum of com-
pound II.
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1028, 640. H NMR spectrum (CDCl3–CD3CN), δ,
ppm: 1.24 m (10H, CH2), 1.50 m (2H, CH2), 1.64 m
(4H, CH2), 1.76 m (4H, CH2), 3.46 s (2H, NCH),
6.80 s (1H, NHfree), 7.18 s (1H, NHassoc), 10.58 s (1H,
NHTf). 13C NMR spectrum (CDCl3–CD3CN), δC, ppm:
23.32 (C4, C4′), 24.24 (C3, C3′, C5, C5′), 30.94 (C2′, C6′),
31.92 (C2, C6), 51.21 (C1′), 53.75 (C1), 119.06 q
(TfNH+, J = 322.4 Hz), 149.36 (C=NTf). 19F NMR
spectrum (CDCl3–CD3CN), δF, ppm: –78.78 (1F, OTf),
–77.94 (1F, HNTf). Found, %: C 35.59; H 4.38;
F 22.15; N 8.18; S 12.42. C15H25F6N3O5S2. Calculated,
%: C 35.64; H 4.98; F 22.55; N 8.31; S 12.68.
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Bis(cyclohexylamino)-N-(trifluoromethylsul-
fonyl)methaniminium bis(trifluoromethylsulfonyl)-
imide (IV). A solution of 0.28 g (1.0 mmol) of bis(tri-
fluoromethanesulfonyl)imide in 3 ml of methylene
chloride was added under vigorous stirring to a solu-
tion of 0.36 g (1.0 mmol) of compound II in 3 ml of
methylene chloride. The mixture was stirred for 6 h at
room temperature, left overnight, and evaporated under
reduced pressure, and the residue (colorless crystals)
was dried under reduced pressure. Yield 0.65 g
(100%), mp 104°C. IR spectrum, ν, cm–1: 3341, 3275,
3133, 2943, 2864, 1676, 1583, 1456, 1337, 1320,
1237, 1207, 1183, 1130, 1062, 942, 653, 597, 506.
1H NMR spectrum (CDCl3–CD3CN), δ, ppm: 1.10–
1.56 m (10H, CH2), 1.64 m (2H, CH2), 1.76 m (4H,
CH2), 1.92 m (4H, CH2), 3.68 s (2H, NCH), 6.71 s
(1H, NHfree), 6.94 s (1H, NHassoc), 8.18 s (1H, NHTf).
13C NMR spectrum (CDCl3–CD3CN), δC, ppm: 23.31
(C4, C4′), 24.29 (C3, C3′, C5, C5′), 30.84 (C2′, C6′), 32.15
(C2, C6), 51.65 (C1′), 54.31 (C1), 119.05 q (TfNH+, J =
322.0 Hz), 119.38 q (Tf2N–, J = 320.9 Hz), 148.75
(C=NTf). 19F NMR spectrum (CDCl3–CD3CN), δF,
ppm: –77.39 (1F), –79.19 (2F). Found, %: C 30.70;
H 3.88; F 26.02; N 8.72; S 14.44. C16H25F9N4O6S3.
Calculated, %: C 30.19; H 3.96; F 26.86; N 8.80;
S 15.11.
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This study was performed under financial support
by the Russian Foundation for Basic Research (project
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 9 2011