A. Jaiyu et al. / Tetrahedron Letters 48 (2007) 1817–1821
1821
Buchanan, A. C.; Holbrey, J. D.; Bridges, N. J.; Rogers,
R. D. Anal. Chem. 2004, 76, 3078–3083; (g) van Leeuwen,
F. W. B.; Beijleveld, H.; Miermans, C. J. H.; Huskens, J.;
Verboom, W.; Reinhoudt, D. N. Anal. Chem. 2005, 77,
122.6 (stilbene-ArC), 122.7 (stilbene-ArC), 129.1 (stilbene-
ArC), 156.1 (stilbene-ArC), 121.4 (CH@CH) FTMS calcd
+
for C H O [ESI, M NH ]: 846.4106, found: 864.4099;
5
4
54
9
4
1
compound m-cis-3: H NMR (400 MHz, CDCl
3.46 (t, OCH CH O-crown, 8H), 3.27, 3.52 (t, ArOCH
CH O-crown, 8H), 3.60 (br, ArOCH CH OAr, 8H), 3.87
3
) d 3.16,
4
611–4617.
2
2
2
-
5
. (a) Reinhoudt, D. N.; Dijkstra, P. J.; in’t Veld, P. J. A.;
Bugge, K.-E.; Harkema, S.; Ungaro, R.; Ghidini, E. J.
Am. Chem. Soc. 1987, 109, 4761–4762; (b) Dijkstra, P. J.;
Brunink, J. A. J.; Bugge, K.-E.; Reinhoudt, D. N.;
Harkema, S.; Ungaro, R.; Ugozzoli, F.; Ghidini, E. J.
Am. Chem. Soc. 1989, 111, 7567–7575; (c) Beer, P. D.;
Gale, P. A.; Chen, Z.; Drew, M. G. B.; Heath, J. A.;
Ogden, M. I.; Powell, H. R. Inorg. Chem. 1997, 36, 5880–
2
2
2
(m, ArCH Ar, 8H), 6.65, 6.91 (t, calix-ArH, 4H), 6.83,
2
6.89 (d, stilbene-ArH, 4H), 7.27 (t, stilbene-ArH, 2H), 6.63
(s, stilbene-ArH, 2H), 6.78 (s, CH@CH, 2H), 7.05, 7.13
1
3
(d, calix-ArH, 8H); C NMR (400 MHz, CDCl ) d 38.1
3
(ArCH
2
Ar), 67.0 (OCH
2
), 68.3 (OCH
2 2
), 68.4 (OCH ), 69.7
(OCH ), 70.7 (OCH
2
2
), 72.8 (OCH
2
), 129.5 (calix-ArC),
129.8 (calix-ArC), 130.0 (calix-ArC), 134.1 (calix-ArC),
134.2 (calix-ArC), 138.5 (calix-ArC), 156.1 (calix-ArC),
158.5 (calix-ArC), 109.9 (stilbene-ArC), 111.5 (stilbene-
ArC), 116.5 (stilbene-ArC), 122.3 (stilbene-ArC), 111.5
(stilbene-ArC), 156.0 (stilbene-ArC), 122.4 (CH@CH);
mp = 206–207 ꢁC; Anal. Calcd for C H O : C, 76.62;
5
893; (d) Bourgeois, J.-P.; Echegoyen, L.; Fibboli, M.;
Pretsch, E.; Diederich, F. Angew. Chem., Int. Ed. 1998, 37,
118–2121.
2
6
7
. (a) Brewer, K. J. Am. Chem. Soc. 1938, 60, 691; (b)
Anderson, C. J.; Welch, M. J. Chem. Rev. 1999, 99, 2219–
5
4
54
9
1
2
234.
H, 6.38. Found: C, 76.68; H, 6.45; compound p-cis-3: H
NMR (400 MHz, CDCl ) d 3.32, 3.39 (t, OCH CH O-
crown, 8H), 3.59 (br, ArOCH CH O-crown, 8H), 3.79 (br,
. (a) Radioactive Waste Management and Disposal;
Cecille, L., Ed.; Elsevier: New York, 1991; (b) Asfari, Z.;
Pulpoka, B.; Saadioui, M.; Wenger, S.; Nierlich, M.;
Thuery, P.; Reynier, N.; Dozol, J.-F.; Vincens, J. In J.
Mol. Recognit. Inclusion, Proc. 9th Int. Symp.; 1998; pp
3
2
2
2
2
ArOCH CH OAr, 8H), 3.92 (s, ArCH Ar, 8H), 6.52, 6.89
2
2
2
(t, calix-ArH, 4H), 6.75, 6.86 (d, stilbene-ArH, 8H), 6.78
1
3
(s, CH@CH, 2H), 7.08, 7.14 (d, calix-ArH, 8H); C NMR
(400 MHz, CDCl ) d 37.8 (ArCH Ar), 68.9 (OCH ), 68.9
1
73–178; (c) Hill, C.; Dozol, J.-F.; Lamare, V.; Rouquette,
3
2
2
H.; Eymard, S.; Tournois, B.; Vincens, J.; Asfari, Z.;
(OCH
2
), 69.4 (OCH
2 2 2
), 70.5 (OCH ), 70.6 (OCH ), 71.9
Bressot, C. J. Inclusion Phenom. Mol. Recognit. Chem.
(OCH
2
), 130.1 (calix-ArC), 130.5 (calix-ArC), 130.6
1
994, 19, 399–408; (d) McDowell, W. J.; Case, G. N.;
McDonough, J. A.; Bartsch, R. A. Anal. Chem. 1992, 64,
013–3017.
(calix-ArC), 131.3 (calix-ArC), 133.8 (calix-ArC), 134.0
(calix-ArC), 155.8 (calix-ArC), 156.4 (calix-ArC), 117.4
(stilbene-ArC), 121.8 (stilbene-ArC), 115.5 (stilbene-ArC),
158.0 (stilbene-ArC), 122.7 (CH@CH); mp = 211 ꢁC;
Anal. Calcd for C H O: C, 76.62; H, 6.38. Found: C,
3
8
. (a) Pipoosananakaton, B.; Sukwattanasinitt, M.; Jaiboon,
N.; Chaichit, N.; Tuntulani, T. Tetrahedron Lett. 2000, 41,
5
4
56
1
9
095–9100; (b) Sukwattanasinitt, M.; Rojanathanes, R.;
76.60; H, 6.38; compound o-cis-4: H NMR (400 MHz,
CDCl ) d 3.12 (t, OCH , 4H) 3.19 (t, OCH , 4H) 3.42 (t,
OCH , 4H), 3.46 (t, OCH , 4H), 3.55 (t, OCH , 4H), 3.61
(m, OCH , 8H), 3.75 (t, ArCH Ar, 8H), 6.41 (s, CH@CH,
Tuntulani, T.; Sritana-anant, Y.; Ruangpornvisuti, V.
Tetrahedron Lett. 2001, 42, 5291–5293; (c) Rojanathanes,
R.; Pipoosananakaton, B.; Tuntulani, T.; Bhanthumna-
vin, W.; Orton, J. B.; Cole, S. J.; Hursthouse, M. B.;
Grossel, M. C.; Sukwattanasinitt, M. Tetrahedron 2005,
3
2
2
2
2
2
2
2
2H), 6.89, 7.02 (d, calix-ArH, 8H), 6.82, 7.09 (t, calix-ArH,
4H), 6.75 (m, stilbene-ArH, 2H), 6.77 (m, stilbene-ArH,
2H), 6.82 (m, stilbene-ArH, 2H), 7.20 (d, stilbene-ArH,
2H); mp = 116–118 ꢁC; Anal. Calcd for C H O : C,
6
1, 1317–1324.
9
. Rojanathanes, R.; Tutulani, T.; Bhabthumnavin, W.;
Sukwattanasinitt, M. Org. Lett. 2005, 7, 3401–3404.
0. Spectroscopic data of stilbene calix[4]arene crown-5 or 6
5
6
58 10
75.53; H, 6.51. Found: C, 75.54; H, 6.56; compound m-cis-
1
1
4: H NMR (400 MHz, CDCl
(t, OCH , 4H), 3.53 (t, OCH
3
) d 3.35 (t, OCH
2
, 8H), 3.46
, 4H),
1
(
3 and 4); compound o-cis-3: H NMR (400 MHz, CDCl
3
)
2
2
, 4H), 3.61 (t, OCH
2
d 3.06, 3.42 (t, –OCH CH O-crown, 8H), 3.11, 3.45
3.64 (t, OCH , 4H), 3.67 (t, OCH , 4H), 3.71 (t, OCH ,
2
2
2
2
2
(
t, ArOCH
CH OAr, 8H), 3.87 (m, ArCH
calix-ArH, 4H), 6.79, 7.18 (d, stilbene-ArH, 4H), 6.90,
2
CH
2
O-crown, 8H), 3.56 (br, ArOCH
2
-
2
4H), 3.85 (s, ArCH Ar, 8) 6.63, 7.27 (t, calix-ArH, 4H),
2
2
Ar, 8H), 6.86, 6.90 (t,
7.07, 7.12 (d, calix-ArH, 8H), 6.82, 6.91 (d, stilben-ArH,
4H), 6.90 (t, stilben-ArH, 2H), 6.64 (s, stilben-ArH, 2H)
1
3
7
7
3
6
1
1
1
.16 (t, stilbene-ArH, 4H), 6.55 (s, CH@CH, 2H), 6.98,
6.78 (s, CH@CH, 2H); C NMR (400 MHz, CDCl ) d
3
1
3
.10 (d, calix-ArH, 8H); C NMR (400 MHz, CDCl
8.1 (ArCH Ar), 68.3 (OCH ), 68.8 (OCH ), 69.7 (OCH
9.8 (OCH ), 70.7 (OCH ), 72.7 (OCH ), 122.8 (calix-ArC),
3
) d
38.0 (ArCH
2
Ar), 61.7 (OCH
2
), 66.9 (OCH
2
), 68.3
),
2
2
2
2
),
(OCH ), 68.9 (OCH
2
2
), 69.4 (OCH
2
), 72.7 (OCH
2
1129.9 (calix-ArC), 130.1 (calix-ArC), 130.3 (calix-ArC),
134.0 (calix-ArC), 134.3 (calix-ArC), 138.5 (calix-ArC),
156.3 (calix-ArC), 158.4 (calix-ArC), 111.3 (stilbene-ArC),
116.4 (stilbene-ArC), 112.4 (stilbene-ArC), 122.6 (stilbene-
2
2
2
23.7 (calix-ArC), 129.2 (calix-ArC), 129.7 (calix-ArC),
33.4 (calix-ArC), 133.9 (calix-ArC), 156.1 (calix-ArC),
56.3 (calix-ArC), 129.1 (stilbene-ArC), 127.9 (stilbene-
ArC), 117.3 (stilbene-ArC), 117.7 (stilbene-ArC), 121.7
stilbene-ArC), 122.8 (stilbene-ArC), 127.9 (stilbene-ArC),
29.1 (stilbene-ArC), 156.9 (stilbene-ArC), 126.7
CH@CH); mp = 124–126 ꢁC; FTMS calcd for C H O
ArC), 122.6 (stilbene-ArC), 156.0 (stilbene-ArC), 122.2
+
(
1
(
(CH@CH) FTMS calcd for C56
H
58
O
10 [ESI, M NH
4
]:
1
908.4368, found: 908.4352; compound p-cis-4: H NMR
(400 MHz, CDCl ) d 3.54 (t, OCH , 4H), 3.81 (t, OCH ,
5
4
54
9
3
2
2
+
[
ESI, M NH ]: 846.4106, found: 864.4091; compound
4H), 3.87 (t, OCH , 4H), 3.91 (t, OCH , 8H), 3.97 (t,
4
2
2
1
o-trans-3: H NMR (400 MHz, CDCl
3
) d 3.16, 3.53
OCH
2
, 4H), 4.46 (t, OCH
2 2
, 4H), 3.87 (s, ArCH Ar, 8H),
(
t, OCH CH O-crown, 8H), 3.25, 3.65 (t, ArOCH
2
2
2
-
6.19, 6.78 (t, calix-ArH, 4H), 7.02, 7.19 (d, calix-ArH, 8H),
CH O-crown, 8H), 3.57, 3.64 (br, ArOCH CH OAr,
7.07, 7.14 (d, stilbene-ArH, 8H), 6.70 (s, CH@CH, 2H)
2
2
2
+
8
8
6
7
H), 3.88 (m, ArCH
2
Ar, 8H), 6.65, 7.15 (d, calix-ArH,
) d 37.9 (ArCH Ar),
), 68.3 (OCH ), 69.8 (OCH ),
0.5 (OCH ), 72.6 (OCH ), 129.3 (calix-ArC), 129.3
mp = 256–257 ꢁC; FTMS calcd for C56
NH
are available in Supplementary data.
58
H O10 [ESI, M
13
H); C NMR (400 MHz, CDCl
5.8 (OCH ), 68.1 (OCH
3
2
4
]: 908.4368, found: 908.4375. The experimental details
2
2
2
2
11. (a) Lamare, V.; Dozol, J. F.; Ugozzoli, F.; Casnati, A.;
Ungaro, R. Eur. J. Org. Chem. 1998, 8, 1559–1568; (b)
Kim, J. S.; Ohki, A.; Ueki, R.; Ishizuka, T.; Shimotashiro,
T.; Maeda, S. Talanta 1999, 48, 705–710.
2
2
(
(
(
calix-ArC), 133.9 (calix-ArC), 134.1 (calix-ArC), 134.1
calix-ArC), 139.3 (calix-ArC), 156.2 (calix-ArC), 158.5
calix-ArC), 111.1 (stilbene-ArC), 115.3 (stilbene-ArC),