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8415
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redissolved in a 25% solution of MeOH in CH2Cl2 and then stirred
overnight in the presence of excess solid NaSbF6. The resultant
suspension was filtered and the solvent removed under reduced
pressure. The resultant solids were suspended in CH2Cl2 and fil-
tered followed by evaporation of the solvent to yield 2$(HSbF6)2
(125 mg, 54%) and 3$(HSbF6)2 (61 mg, 19%) as colourless solids.
Thread 2$(HSbF6)2: 1H NMR (400 MHz, CD2Cl2)
d¼1.13–1.29 (m,
´
Angew. Chem., Int. Ed. 2004, 43, 2661–2665; (e) Perez, E. M.; Dryden, D. T. F.;
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30H, 6ꢀCH2, 6ꢀCH3), 1.35 (m, 2H, CH2), 1.52 (m, 2H, CH2), 1.67
(m, 2H, CH2), 2.45 (m, 2H, CH2), 2.90 (br m, 2H, CH2CH2N), 2.97 (br
m, 2H, CH2CH2N), 3.90 (t, 2H, J¼6.5, CH2O), 3.92 (t, 1H, J¼7.9,
Ph2CHCH2), 4.07 (br t, 2H, ArCH2N), 4.15 (br t, 2H, ArCH2N), 6.85 (d,
2H, J¼8.5, ArH), 7.10–7.26 (m, 14H, ArH), 7.46 (s, 1H, ArH); 13C NMR
´
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(100 MHz, CD2Cl2)
d
¼25.9, 26.38, 26.45, 28.97, 29.01, 29.1, 29.2,
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29.3, 30.1, 31.4, 31.7, 35.3, 48.8, 49.0, 50.0, 51.5, 52.6, 68.5, 115.9,
121.2, 124.3,124.9, 127.4, 127.8, 128.8, 129.4, 131.6, 143.1, 153.1, 161.0;
HRMS (FAB) C48H68N2O calcd m/z [(MþH)þ]¼689.5410, found
689.5412. Rotaxane 3$(HSbF6)2: 1H NMR (400 MHz, CD2Cl2)
d
¼1.01–1.38 (m, 32Hþ32H0, 6ꢀCH2, 6ꢀCH3, 6ꢀCH02, 6ꢀCH03), 1.30–
1.71 (m, 4Hþ4H0, 2ꢀCH2, 2ꢀCH02), 2.02 (m, 2H0, CH02), 2.45 (m, 2H,
CH2), 2.91 (br m, 4H, 2ꢀCH2), 3.08 (br m, 2H0, CH02), 3.25 (br m, 2H0,
CH02), 3.32 (t, H0, J¼7.6, Ph2CH0), 3.33–3.44 (m, 4Hþ4H0,
OCH2þOCH02 diastereotopic signals), 3.46–3.56 (m, 4Hþ4H0,
OCH2þOCH02 diastereotopic ethylene signals), 3.57–3.83 (m,
10Hþ8H0, OCH2þOCH02 diastereotopic ethylene signals OCH2), 3.87
(t, 2H0, J¼6.6, OCH02), 3.93 (t, 1H, J¼8.0, Ph2CH0), 3.96–4.19 (m,
8Hþ12H0, OCH2þOCH02 diastereotopic ethylene signals 2ꢀArCH02),
4.41 (m, 2H, ArCH2), 4.63 (m, 2H, ArCH2), 6.43 (d, 2H, J¼8.7, ArH),
6.64 (m, 4H0, ArH0), 6.71 (m, 4H, ArH), 6.82 (m, 4H, ArH), 6.85–6.90
(m, 6H0, ArH0), 6.96 (m, 4H0, ArH0), 7.00 (d, 2H, J¼8.7, ArH), 7.03–7.15
(m, 2Hþ8H0, ArHþArH0), 7.18–7.25 (m, 10H, ArH), 7.29–7.32 (m,
Hþ2H0, ArHþArH0), 7.43 (s, H0, ArH0); 13C NMR (100 MHz, CDCl3)
´
4. (a) Leigh, D. A.; Perez, E. M. Chem. Commun. 2004, 2262–2263; (b) Abraham,
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(major translational isomer)
d
¼25.5, 26.1, 26.4, 28.4, 28.6, 28.8,
´
2004, 10, 6375–6392; (d) Marlin, D. S.; Gonzalez Cabrera, D.; Leigh, D. A.;
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4.3. Deprotonation of 2$(HSbF6)2 and 3$(HSbF6)2
In a disposable polypropylene reaction tube fitted with a frit and
a tap, diethylaminopolystyrene resin (200 mg, 0.2 molar equiv) was
swelled in CH2Cl2 and the excess solvent drained off. A solution of
2$(HSbF6)2 or 3$(HSbF6)2 (2 mmol) in CH2Cl2 (2 ml) was added and
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and evaporated to give 2$HSbF6 or 3 with >95% recovery of
material.
´
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Acknowledgements
This work was supported by the EPSRC. D.A.L. is an EPSRC Senior
Research Fellow and holds a Royal Society-Wolfson Research Merit
Award. We thank the EPSRC National Mass Spectrometry Service
Centre (Swansea, UK) for accurate mass data.
´
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Supplementary data
9. Tokunaga, Y.; Akasaka, K.; Hisada, K.; Shimomura, Y.; Kakuchi, S. Chem. Com-
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Supplementary data associated with this article can be found in
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