(t, J = 6.8 Hz, 6 H); 13C NMR (100 MHz CDCl3): δ 14.1, 19.3,
5 (a) A. M. Barrios and S. J. Lippard, J. Am. Chem. Soc., 2000, 122, 9172;
(b) A. M. Barrios and S. J. Lippard, J. Am. Chem. Soc., 1999, 121,
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Chem.–Eur. J., 1999, 5, 1617; (d) C. He and S. J. Lippard, J. Am. Chem.
Soc., 2000, 122, 184.
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E. Nordlander, Inorg. Chem., 2004, 43, 8252.
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K. Takahashi and H. Okawa, Inorg. Chem., 1998, 37, 989;
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111, 4497.
22.6, 28.4, 28.6, 31.4, 65.2, 77.5.
1
Icosa-9,11-diyne.17 Colorless oil (47%): H NMR (400 MHz,
CDCl3): δ 2.23(t, J = 7.2 Hz, 4 H), 1.46–1.53 (m, 4 H),
1.26–1.40 (m, 20 H), 0.87 (t, J = 6.8 Hz, 6 H); 13C NMR
(100 MHz, CDCl3): δ 14.2, 19.3, 22.7, 28.4, 28.9, 29.1, 29.2,
31.9, 65.3, 77.6.
Tetracosa-11,13-diyne.19 Colorless oil (59%): 1H NMR
(400 MHz, CDCl3): δ 2.22 (t, J = 6.8 Hz, 4 H), 1.46–1.53 (m, 4
H), 1.24–1.37 (m, 14 H), 0.86 (t, J = 6.8 Hz, 6 H); 13C NMR
(100 MHz, CDCl3): δ 14.5, 19.6, 23.1, 28.7, 29.2, 29.6, 29.8,
29.9, 30.0, 32.2, 65.3, 77.5.
Crystallography
8 S. Lin and T. Agapie, Synlett, 2010, 1.
Crystals suitable for X-ray determination were obtained for 3
and (4+4′) by recrystallization from methanol/CH2Cl2 at room
temperature. Cell parameters were determined by a Siemens
SMART CCD diffractometer. The structure was solved using the
SHELXS-97 program20 and refined using the SHELXL-97
program21 by full-matrix least-squares on F2 values.
Crystal data for 3: C18H22Cl8N6Ni2O2, Fw = 755.44, Monocli-
nic, P21/n, a = 10.9327(6) Å, b = 16.7419(6) Å, c = 16.6176(9)
Å, α = 90, β = 93.925(5)°, γ = 90, V = 3034.5(3) Å3, Z = 4, Dc
= 1.654 Mg m−3, F(000) = 1520, crystal size: 0.25 × 0.20 ×
0.10 mm3, 3.07 to 27.49°, 22170 reflections collected, 6957
reflection [R(int) = 0.0453], Final R indices [I > 2σ(I)]: R1 =
0.0592, wR2 = 0.1764, for all data R1 = 0.0955, wR2 = 0.1878,
Goodness-of-fit on F2 = 1.125.
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W.-H. Sun, Inorg. Chim. Acta, 2011, 370, 215; (b) A. Velian, S. Lin,
A. J. M. Miller, M. W. Day and T. Agapie, J. Am. Chem. Soc., 2010, 132,
6296; (c) A. P. Armitage, Y. D. M. Champouret, H. Grigoli,
J. D. A. Pelletier, K. Singh and G. A. Solan, Eur. J. Inorg. Chem., 2008,
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2008, 27, 5911; (e) B. A. Rodriguez, M. Delferro and T. J. Marks,
Organometallics, 2008, 27, 2166; (f) D. Meinhard, P. Reuter and
B. Rieger, Organometallics, 2007, 26, 751; (g) K. N. Green,
S. P. Jeffery, J. H. Reibenspies and M. Y. Darensbourg, J. Am. Chem.
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T. Kawai, K. Tanaka, T. Kitagawa and M. Suzuki, Inorg. Chem., 2006,
45, 2873.
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V. V. Strelets, E. Nordlander and A. A. Shteinman, Dalton Trans., 2006,
492; (b) W.-Z. Lee, H.-S. Tseng, T.-L. Wang, H.-L. Tsai and T.-S. Kuo,
Organometallics, 2010, 29, 2874.
11 E. Jabri, M. B. Carr, R. P. Hausinger and P. A. Karplus, Science, 1995,
268, 998.
12 S. W. Jin, B. Liu and W. Z. Chen, Chin. Chem. Lett., 2007, 18, 383.
13 Y.-H. Chang, Z.-Y. Liu, Y.-H. Liu, S.-M. Peng, J.-T. Chen and S.-T. Liu,
Dalton Trans., 2011, 40, 489.
14 (a) G. R. Newkome, S. J. Garbis, V. K. Majestic, F. R. Fronczek and
G. Chiari, J. Org. Chem., 1981, 46, 833; (b) N. Kitajim, K. Fujisawa,
C. Fujimoto, Y. Moro-oka, S. Hashimoto, T. Kitagawa, K. Toriumi,
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(c) P. Govindaswamy, Y. A. Mozharivskyj and M. R. Kollipara,
J. Organomet. Chem., 2004, 689, 3265.
Crystal data for (4+4′): C68H106Cl16N18Ni6O12, Fw = 2287.17,
Trigonal, P3221, a = 14.76480(10) Å, b = 14.76480(10) Å, c =
36.4182(6) Å, α = 90°, β = 90°, γ = 120°, V = 6875.50(13) Å3,
Z = 3, Dc = 1.657 Mg m−3, F(000) = 3528, crystal size: 0.20 ×
0.15 × 0.10 mm3, 2.98 to 27.49°, 42248 reflections collected,
10505 reflections [R(int) = 0.0401], Goodness-of-fit on F2
=
1.124, Final R indices [I > 2σ(I)]: R1 = 0.0541, wR2 = 0.1542,
for all data R1 = 0.0603, wR2 = 0.1587.
Acknowledgements
15 For reviews, see: (a) P. Siemsen, R. C. Livingston and F. Diederich,
Angew. Chem., Int. Ed., 2000, 39, 2632; (b) S. Adimurthy, C. C. Malakar
and U. Beifuss, J. Org. Chem., 2009, 74, 5648; (c) S. Yamazaki, Inorg.
Chim. Acta, 2011, 366, 1 and references therein.
This work was supported by the National Science Council,
Taiwan, for the financial support (NSC97-2113-M002-013).
16 Z. Chen, H. Jiang, A. Wang and S. Yang, J. Org. Chem., 2010, 75, 6700.
17 J. H. Li, Y. Liang and Y. X. Xie, J. Org. Chem., 2005, 70, 4393.
18 D. Wang, J. Li, N. Li, T. Gao, S. Hou and B. Chen, Green Chem., 2010,
12, 45.
Notes and references
1 F. Meyer, Prog. Inorg. Chem., 2009, 56, 487.
2 M. T. Kieber-Emmons and C. G. Riordan, Acc. Chem. Res., 2007, 40,
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19 A. Lei, M. Srivastava and X. Zhang, J. Org. Chem., 2002, 67, 1969.
20 G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 1990,
46, 467.
3 V. Beck and D. O’Hare, J. Organomet. Chem., 2004, 689, 3920.
4 R. P. Hausinger, Biochemistry of Nickel, Plenum Press, New York, 1993.
21 G. M. Sheldrick, SHELXL-97, University of Göttingen, Göttingen,
Germany, 1997.
This journal is © The Royal Society of Chemistry 2012
Dalton Trans., 2012, 41, 3468–3473 | 3473