References and Notes
<A NAME="RW11905ST-1">1</A>
Diederich F.
Cyclophanes
The Royal Society of Chemistry;
Cambridge:
1991.
<A NAME="RW11905ST-2">2</A>
Lehn JM.
Supramolecular Chemistry, Concepts and Perspectives
VCH;
Weinheim:
1995.
<A NAME="RW11905ST-3">3</A>
Purse BW.
Rebek J.
Proc. Natl. Acad. Sci. U.S.A.
2005,
102:
10777
<A NAME="RW11905ST-4A">4a</A>
Rebek J.
Science
1987,
235:
1478
<A NAME="RW11905ST-4B">4b</A>
Shimizu KD.
Dewey TM.
Rebek J.
J. Am. Chem. Soc.
1994,
116:
5145
<A NAME="RW11905ST-4C">4c</A>
Warrener RN.
Margetic D.
Amarasekara AS.
Butler DN.
Mahadevan IB.
Russell RA.
Org. Lett.
1999,
1:
199
<A NAME="RW11905ST-5">5</A>
Adrian JC.
Wilcox CS.
J. Am. Chem. Soc.
1989,
111:
8055
<A NAME="RW11905ST-6">6</A>
Sanderson PEJ.
Kilburn JD.
Still WC.
J. Am. Chem. Soc.
1989,
111:
8314
<A NAME="RW11905ST-7">7</A>
Chen CW.
Whitlock HW.
J. Am. Chem. Soc.
1978,
100:
4921
<A NAME="RW11905ST-8">8</A>
Zimmerman SC.
VanZyl CM.
J. Am. Chem. Soc.
1987,
109:
7894
<A NAME="RW11905ST-9">9</A>
Zimmerman SC.
Wu W.
J. Am. Chem. Soc.
1989,
111:
8054
<A NAME="RW11905ST-10">10</A>
Klärner FG.
Kahlert B.
Acc. Chem. Res.
2003,
36:
919
<A NAME="RW11905ST-11">11</A>
Harmata M.
Acc. Chem. Res.
2004,
37:
862
<A NAME="RW11905ST-12A">12a</A>
Klärner FG.
Lobert M.
Naatz U.
Bandmann H.
Boese R.
Chem.-Eur. J.
2003,
9:
5036
<A NAME="RW11905ST-12B">12b</A>
Wu A.
Chakraborty A.
Fettinger JC.
Flowers RA.
Isaacs L.
Angew. Chem. Int. Ed.
2002,
41:
4028
<A NAME="RW11905ST-13">13</A>
Dixon RP.
Geib SJ.
Hamilton AD.
J. Am. Chem. Soc.
1992,
114:
365
<A NAME="RW11905ST-14A">14a</A>
Paliwal S.
Geib S.
Wilcox CS.
J. Am. Chem. Soc.
1994,
116:
4497
<A NAME="RW11905ST-14B">14b</A>
Lagona J.
Fettinger JC.
Isaacs L.
Org. Lett.
2003,
5:
3745
<A NAME="RW11905ST-15A">15a</A>
Sijbesma RP.
Nolte RJM.
J. Org. Chem.
1991,
56:
3122
<A NAME="RW11905ST-15B">15b</A>
Sijbesma RP.
Wijmenga SS.
Nolte RJM.
J. Am. Chem. Soc.
1992,
114:
9807
<A NAME="RW11905ST-15C">15c</A>
Sijbesma RP.
Kentgens APM.
Lutz ETG.
van der Maas JH.
Nolte RJM.
J. Am. Chem. Soc.
1993,
115:
8999
<A NAME="RW11905ST-15D">15d</A>
Reek JNH.
Priem AH.
Engelkamp H.
Rowan AE.
Elemans JAAW.
Nolte RJM.
J. Am. Chem. Soc.
1997,
119:
9956
<A NAME="RW11905ST-15E">15e</A>
Rowan AE.
Elemans JAAW.
Nolte RJM.
Acc. Chem. Res.
1999,
32:
995
<A NAME="RW11905ST-15F">15f</A>
Jansen RJ.
de Gelder R.
Rowan AE.
Scheeren HW.
Nolte RJM.
J. Org. Chem.
2001,
66:
2643
<A NAME="RW11905ST-16">16</A>
Savostianoff DFr. inventors; Patent Appl. 2 291 203.
; Chem. Abstr. 1977, 86, 121377n
<A NAME="RW11905ST-17">17</A>
Mock WL.
Manimaran T.
Freeman WA.
Kuksuk RM.
Maggio JE.
Williams DH.
J. Org. Chem.
1985,
50:
60
<A NAME="RW11905ST-18">18</A>
Liu S.
Wu X.
Zhang S.
Yao J.
Liang F.
Wu C.
New J. Chem.
2004,
28:
562
<A NAME="RW11905ST-19">19</A>
Burnett CA.
Logona J.
Wu A.
Shaw JA.
Coady D.
Fettinger JC.
Day AI.
Isaacs L.
Tetrahedron
2003,
59:
1961
<A NAME="RW11905ST-20">20</A>
Smeets JWH.
Sijbesma RP.
Niele FGM.
Spek AL.
Smeets WJJ.
Nolte RJM.
J. Am. Chem. Soc.
1987,
109:
928
<A NAME="RW11905ST-21">21</A>
Nunen JLM.
Nolte RJM.
J. Chem. Soc., Perkin Trans. 2
1997,
1473
<A NAME="RW11905ST-22">22</A>
Compound 4a: IR (KBr): 3457 (m), 2850 (m), 1762 (s), 1731 (s), 1464 (m), 1419 (m), 1389 (m),
1251 (s), 1173 (m), 1054 (m), 950 (m), 761 (m), 699 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.12 (t, 4 H), 6.94-6.88 (m, 6 H), 5.49 (d, 4 H, J = 13.2 Hz), 4.56 (d, 4 H, J = 13.2 Hz), 4.33 (q, 4 H, J = 6.8 Hz), 1.35 (t, 6 H, J = 6.8 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.13, 157.32, 145.86, 129.24, 121.71, 117.73, 76.13, 63.33, 58.31, 13.84.
MS: m/z (%) = 521 (100) [M+], 416 (68), 387 (95), 343 (61), 240 (31), 105 (93).
Compound 4b: IR (KBr): 3456 (m), 2861 (m), 1763 (s), 1731 (s), 1522 (m), 1465 (m), 1418 (m),
1392 (m), 1247 (s), 1176 (m), 1052 (m), 944 (m), 809 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 6.92 (d, 4 H), 6.83 (d, 4 H), 5.43 (d, 4 H, J = 13.2 Hz), 4.53 (d, 4 H, J = 13.2 Hz), 4.32 (q, 4 H, J = 6.8 Hz), 2.24 (s, 6 H), 1.34 (t, 6 H, J = 6.8 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.18, 157.30, 143.58, 130.92, 129.73, 117.92, 76.09, 63.26, 58.51, 20.44,
13.81. MS: m/z (%) = 549 (100) [M+], 400(91), 356 (41), 118 (88).
Compound 4c: IR (KBr): 3453 (m), 2919 (m), 2847 (m), 1765 (s), 1727 (s), 1465 (m), 1412 (m),
1384 (m), 1248 (s), 1158 (m), 1057 (m), 936 (m), 782 (m), 701 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.04 (2 H), 6.80-6.72 (m, 6 H), 5.46 (d, 4 H, J = 13.2 Hz), 4.51 (d, 4 H, J = 13.2 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 2.20 (s, 6 H), 1.35 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.22, 157.44, 145.98, 139.00, 128.98, 122.84, 118.81, 115.03, 76.09, 63.34,
58.68, 21.44, 13.87. MS: m/z (%) = 549 (100) [M+], 400(97), 356 (49), 118 (60).
Compound 4d: IR (KBr): 3451 (s), 2987 (m), 2939 (m), 1768 (s), 1729 (s), 1515 (s), 1463 (m),
1416 (m), 1284 (m), 1242 (s), 1179 (m), 1032 (m), 824 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 6.93 (d, 4 H, J = 8.8 Hz), 6.71 (d, 4 H, J = 8.8 Hz), 5.34 (d, 4 H, J = 12.8 Hz), 4.53 (d, 4 H, J = 12.8 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 3.73 (s, 6 H), 1.34 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.21, 157.48, 154.91, 139.73, 120.12, 114.40, 76.05, 63.27, 59.32, 55.20,
13.83. MS: m/z (%) = 581 (100)[M+], 416 (41), 372 (26), 191 (27), 176 (30), 134 (99), 120 (71).
Compound 4e: IR (KBr): 3457 (m), 2962 (m), 1753 (s), 1737 (s), 1261 (s), 1093 (s), 1050 (s),
802 (s) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.05 (d, 4 H, J = 8.8 Hz), 6.90 (d, 4 H, J = 8.8 Hz), 5.41 (d, 4 H, J = 12.8 Hz), 4.49 (d, 4 H, J = 12.8 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 2.78-2.82 (m, 2 H), 1.34 (d, 6 H, J = 7.2 Hz), 1.18 (d, 12 H, J = 2.4 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.32, 157.63, 144.01, 142.63, 127.13, 118.49, 76.14, 63.33, 59.20, 33.21,
23.95, 13.92. MS: m/z (%) = 605 (100) [M+], 428 (74), 385 (45), 287 (28), 202 (28), 146 (40), 132 (83).
Compound 4f: IR (KBr): 3411 (s), 1765 (s), 1722 (s), 1498 (m), 1468 (m), 1415 (s), 1238 (s),
1048 (m), 903 (m), 833 (m), 717 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.02 (d, 4 H, J = 8.8 Hz), 6.82 (d, 4 H, J = 8.8 Hz), 5.48 (d, 4 H, J = 14.0 Hz), 4.62 (d, 4 H, J = 14.0 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 1.35 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 164.93, 157.10, 144.22, 129.21, 126.47, 118.46, 76.20, 63.53, 57.61, 13.87.
MS: m/z (%) = 590 (100) [M+], 538 (21), 420 (70), 376 (27), 202 (25), 191 (9), 189 (21), 145 (65).
Compound 4g: IR (KBr): 3448 (m), 2981 (w), 2936 (w), 1746 (s), 1726 (s), 1496 (m), 1467 (m),
1417 (m), 1280 (m), 1239 (s), 1094 (m), 1047 (m), 975 (m), 908 (m), 818 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.18 (d, 4 H, J = 8.8 Hz), 6.77 (d, 4 H, J = 8.8 Hz), 5.48 (d, 4 H, J = 14.0 Hz), 4.62 (d, 4 H, J = 14.0 Hz), 4.34 (q, 4 H, J = 7.2 Hz), 1.35 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 164.87, 157.04, 144.77, 132.15, 118.88, 113.93, 76.16, 63.51, 57.53, 13.86.
MS: m/z (%) = 679 (73) [M+], 467 (58), 466 (10), 464 (66), 423 (30), 420 (26), 409 (4), 243 (10), 241 (24),
240 (63), 182 (100).
Compound 4h: IR (KBr): 3426 (m), 1749 (s), 1727 (s), 1493 (m), 1466 (m), 1417 (m), 1279 (m),
1245 (s), 1174 (m), 1093 (m), 909 (m), 812 (m), 694 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.37 (d, 4 H, J = 7.6 Hz), 6.66 (d, 4 H, J = 7.6 Hz), 5.47 (d, 4 H, J = 14.0 Hz), 4.61 (d, 4 H, J = 14.0 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 1.34 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 164.95, 157.11, 145.62, 138.20, 119.46, 84.29, 76.24, 63.56, 57.62, 13.94.
MS: m/z (%) = 723 (93) [M+], 647 (13), 513 (70), 387 (18), 231 (100), 208 (48).
<A NAME="RW11905ST-23">23</A> Crystal data for compound 4d: C28H32N6O8, M = 580.60, triclinic, a = 7.5266 (18), b = 13.438 (3), c = 14.167 (3) Å, a = 87.547 (4)°, β = 83.627 (4)°, γ = 81.942 (4)°, U = 1409.4 (6) Å3, T = 292 (2) K, space group P-1, Z = 2, µ (Mo-Kα) = 0.102 mm-1, 7110 reflections measured, 4870 unique (R
int = 0.0216) which were used in all calculations. The final wR
2 (F
2) was 0.1816 (all data). CCDC-281947 contains the supplementary crystallographic data
for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html
[or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2
1EZ, UK; fax: +44(1223)336033; email: deposit@ccdc.cam.ac.uk]