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M. Albrecht et al.
LETTER
(ESI+): m/z = 387 [M + H]+. Anal. Calcd for
C23H18O4N2·0.66H2O: C, 69.34; H, 4.89; N, 7.03. Found: C,
69.21; H, 4.76; N, 6.92.
References and Notes
(1) Hollingshead, R. G. W. Oxine and its Derivatives;
Butterworth: London, 1954.
(11) Characterization of K2[(11)2Zn2]: 1H NMR (300 MHz,
DMSO-d6): d = 8.45 (d, J = 8.2 Hz, 1 H), 8.34 (m, 1 H), 7.96
(m, 2 H), 7.53 (d, J = 8.2 Hz, 1 H), 7.36 (m, 2 H), 6.92 (m, 2
H), 4.81 (s, 1 H). 4.18 (s, 1 H); the signals of the benzylic
protons are hidden under the solvent and water peaks. MS
(ESI+): m/z = 899 [M + H]+. Anal. Calcd for
(2) (a) Pohl, R.; Montes, V. A.; Shinar, J.; Anzenbacher, P. Jr. J.
Org. Chem. 2004, 69, 1723. (b) VanDeun, R.; Fias, P.;
Nockemann, P.; Schepers, A.; Parac-Vogt, T.; VanHecke,
K.; VanMeervelt, L.; Binnemans, K. Inorg. Chem. 2004, 43,
8461. (c) Imbert, D.; Comby, S.; Chauvin, A.-S.; Bünzli, J.-
C. G. Chem. Commun. 2005, 1432.
(3) (a) Albrecht, M.; Blau, O. Synthesis 1997, 213. For reviews
on helicates, see: (b) Piguet, C.; Bernardinelli, G.;
Hopfgartner, G. Chem. Rev. 1997, 97, 2005. (c) Albrecht,
M. Chem. Rev. 2001, 101, 3457. (d) Hannon, M. J.; Childs,
L. J. Supramol. Chem. 2004, 16, 7.
(4) Hiratani, K.; Takahashi, T.; Kasuga, K.; Sugihara, H.;
Fujiwara, K.; Ohashi, K. Tetrahedron Lett. 1995, 36, 5567.
(5) Albrecht, M.; Blau, O.; Wegelius, E.; Rissanen, K. New J.
Chem. 1999, 667.
(6) Albrecht, M.; Blau, O.; Fröhlich, R. Proc. Natl. Acad. Sci.
U.S.A. 2002, 99, 4876.
C46H30O8N4Zn2K2·5H2O: C, 51.84; H, 3.78; N, 5.26. Found:
C, 51.82; H, 3.37; N, 4.95.
(12) (a) Rb2[(11)2Zn2]: 1H NMR (300 MHz, DMSO-d6): d = 8.31
(m, 3 H), 7.92 (d, J = 8.2 Hz, 1 H), 7.54 (dd, J = 8.2, 4.7 Hz,
1 H), 7.35 (m, 2 H), 6.85 (m, 2 H), 4.43 (m, 2 H). 3.78 (d,
J = 15.3 Hz, 1 H), 3.36 (d, J = 8.7 Hz, 1 H); two further
signals are hidden under the water peak. (b) X-ray crystal
structure analysis: formula Rb2(CH3OH)3 (H2O)·
[(C23H15N2O4)2Zn2]·CH3OH, M = 1214.60, yellow-orange
crystal 0.30 × 0.30 × 0.05 mm, a = 12.944 (1), b = 13.320
(1), c = 15.608 (1) Å, a = 101.26 (1), b = 107.06 (1),
g = 99.84 (1)°, V = 2447.2 (3) Å3, rcalcd = 1.648 gcm–3,
m = 0.303 mm–1, empirical absorption correction (0.464 £ T
£ 0.863), Z = 2, triclinic, space group P1bar (No. 2),
l = 0.71073 Å, T = 198 K, w and j scans, 25862 reflections
collected ( h, k, l), [(sinq)/l] = 0.67 Å–1, 11911
independent (Rint = 0.051) and 8202 observed reflections
[I ≥ 2 s(I)], 656 refined parameters, R = 0.047, wR2 = 0.100,
max. residual electron density 0.72 (–0.57) eÅ–3, hydrogen
atoms are calculated and refined. (c) Data set was collected
with a Nonius Kappa CCD diffractometer, equipped with a
rotating anode generator, COLLECT (Nonius B.V., 1998).
(d) Data reduction, Denzo-SMN: Otwinowski, Z.; Minor,
W. Methods Enzymol. 1997, 276, 307. (e) Absorption
correction, Denzo: Otwinowski, Z.; Borek, D.; Majewski,
W.; Minor, W. Acta Crystallogr., Sect. A 2003, 59, 228.
(f) Structure solution, SHELXS-97: Sheldrick, G. M. Acta
Crystallogr., Sect. A 1990, 46, 467. (g) Structure
(7) Piguet, C.; Hopfgartner, G.; Bocquet, B.; Schaad, O.;
Williams, A. F. J. Am. Chem. Soc. 1994, 116, 9092.
(8) Shrader, W. D.; Celebuski, J.; Kline, S. I.; Johnson, D.
Tetrahedron Lett. 1988, 29, 1351.
(9) Characterization of 5: 1H NMR (300 MHz, CDCl3): d = 8.22
(d, J = 8.2 Hz, 2 H), 7.69 (t, J = 8.2 Hz, 2 H), 7.67 (d, J = 8.2
Hz, 2 H), 7.44 (d, J = 8.2 Hz, 2 H), 7.40 (br d, J = 7.7 Hz, 2
H), 5.59 (s, 2 H), 5.09 (s, 4 H). MS (EI): m/z = 392 [M + H]+.
Characterization of 6: 1H NMR (300 MHz, CDCl3): d = 8.28
(d, J = 8.4 Hz, 1 H), 7.62 (t, J = 8.2 Hz, 1 H), 7.48 (d, J = 8.2
Hz, 1 H), 7.40 (d, J = 8.4 Hz, 1 H), 7.23 (br d, J = 7.4 Hz, 1
H), 5.49 (s, 1 H), 5.48 (s, 1 H), 4.97 (s, 2 H), 4.33 (s, 2 H).
MS (EI): m/z = 223 [M + H]+. Characterization of 7: 1H NMR
(300 MHz, CDCl3): d = 10.07 (s, 2 H), 8.50 (d, J = 8.5 Hz, 2
H), 7.92 (d, J = 8.2 Hz, 2 H), 7.51 (d, J = 8.2 Hz, 2 H), 7.44
(d, J = 8.5 Hz, 2 H), 4.66 (s, 2 H), 3.53 (s, 4 H).
Characterization of 8: 1H NMR (300 MHz, DMSO-d6):
d = 8.39 (d, J = 8.7 Hz, 2 H), 8.14 (d, J = 8.4 Hz, 2 H), 7.51
(d, J = 8.24, 2 H), 7.44 (d, J = 8.5 Hz, 2 H), 4.66 (s, 2 H),
3.53 (s, 4 H). MS (EI): m/z = 427.3 [M + H]+.
refinement: Sheldrick, G. M. SHELXL-97; Universität
Göttingen: Germany, 1997. (h) Graphics: Keller, E.
SCHAKAL; Universität Freiburg: Germany, 1997.
(i) CCDC 294394 contains the supplementary
(10) Characterization of 9: 1H NMR (300 MHz, CDCl3): d = 8.92
(dd, J = 8.4, 1.8 Hz, 1 H), 8.22 (d, J = 8.5 Hz, 1 H), 8.12 (dd,
J = 8.2, 1.8 Hz, 1 H), 7.69 (d, J = 8.3 Hz, 1 H), 7.40 (m, 7 H),
5.58 (s, 2 H), 5.11 (s, 2 H), 5.05 (s, 2 H). Characterization of
10: 1H NMR (300 MHz, CDCl3): d = 8.75 (dd, J = 4.4, 1.6
Hz, 1 H), 8.24 (d, J = 8.3 Hz, 1 H), 8.10 (dd, J = 8.2, 1.4 Hz,
1 H), 7.94 (br s, 1 H), 7.65 (d, J = 8.6 Hz, 1 H), 7.57 (d,
J = 8.6 Hz, 1 H), 7.30 (m, 4 H), 4.91 (s, 1 H), 4.86 (s, 1 H),
3.67 (s, 2 H), 3.65 (s, 2 H). Characterization of 11-H3: Mp
136 °C. 1H NMR (300 MHz, DMSO-d6): d = 8.81 (dd,
J = 4.2, 1.7 Hz, 1 H), 8.48 (d, J = 8.4 Hz, 1 H), 8.27 (dd,
J = 8.4, 1.5 Hz, 1 H), 8.08 (d, J = 8.2 Hz, 1 H), 7.48 (m, 3 H),
7.35 (s, 2 H), 4.70 (s, 2 H), 3.58 (s, 2 H), 3.55 (s, 2 H). MS
crystallographic data for this paper. These data can be
retrieving.html [or from the Cambridge Crystallographic
Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax:
+44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
(13) Piguet, C.; Hopfgartner, G.; Williams, A. F.; Bünzli, J.-C. G.
J. Chem. Soc., Chem. Commun. 1995, 491.
(14) See for example: (a) Piguet, C.; Hopfgartner, G.; Williams,
A. F.; Bünzli, J.-C. G. J. Chem. Soc., Chem. Commun. 1995,
491. (b) Petitjean, A.; Kyritsakas, N.; Lehn, J.-M. Chem.
Eur. J. 2005, 11, 6818. (c) Albrecht, M.; Fröhlich, R. J. Am.
Chem. Soc. 1997, 119, 1656.
Synlett 2006, No. 6, 924–926 © Thieme Stuttgart · New York