H. Zhang et al. / Tetrahedron 69 (2013) 3656e3663
3663
4.2.18. Final product F2.
4.2.20. Final product F3.
Conversion of I3 (0.562 g, 0.54 mmol) with 1-aminododecan
(0.201 g, 1.08 mmol). dH (CDCl3) 11.84 (2H, s, NH5), 9.37 (2H, H11),
7.98 (4H, d, H3), 7.71 (2H, d, H9), 7.51 (2H, d, H8), 6.98 (4H, d, H200),
0
6.37 (2H, t, NH6), 4.34 (4H, t, Ha ), 4.02 (4H, t, Ha), 3.47 (4H,00q, Ha ),
Conversion of I2 (0.182 g, 0.238 mmol) with 1-aminododecan
(0.0883 g, 0.476 mmol). dH (CDCl3) 12.17 (1H, s, NH13), 11.44 (1H,
s, NH5), 9.31 (1H, s, H19), 9.01 (1H, s, H11), 8.02 (2H, d, H3), 7.66
(1H, t, NH6), 7.36 (3H, H8,9,16), 07.21 (1H, d, H17), 7.20 (1H, t, NH1400),
7.02 (2H, d, H2), 4.38(2H, t, Ha ), 004.05 (2H, t, Ha), 3.63 (2H, q, Ha ),
0
00
0
0
00
1.80 (8H, Hb,b ), 1.65 (4H, Hb ), 1.5e1.2 (72H, Hcee,c ef ,c ef ), 0.88
0
00
(12H, Hg ,g ); dC (CDCl3) 168.58 (C6), 165.87 (C21), 165.20 (C5), 162.28
(C1), 139.87 (C12), 133.85 (C10), 129.30 (C3), 126.55 (C4,8), 124.33 (C7),
0
123.43 (C9), 122.46 (C11), 114.49 (C2)0, 68.21 (Ca), 65.64 (Ca ), 40.28
00
0
00
0
00 00
00
0
000
a000
(Ca ), 31.89 (Ce ,e ), 30.0e28.6 (Cb,d,e,b ,d ,b ,d ), 27.02 (Cc ), 25.98 and
3.52 (2H,00q,00H ), 1.85 (6H, Hb,b ,b ), 1.7300(0 2H, m, Hb ), 1.5e1.2 (72H,
0
0
00
0
00
0
0
0
00
000ef000
25.91 (Cc,c ), 22.66 (Cf ,f ), 14.07 (Cg ,g ). Anal. Calcd for C88H138N4O10
C 74.85, H 9.85, N 3.97. Found: C 76.11, H 10.71, N 3.92.
:
Hcef,c ef ,c ef ,c
), 0.87 (12H, Hg,g ,g ,g ); dC (CDCl3) 169.00 (C6),
168.66 (C14), 167.45 (C21), 164.91 (C5), 162.87 (C13), 162.46 (C1),
139.30 (C20), 138.28 (C12), 136.39 (C10), 132.95 (C18), 129.43 (C3),
128.00 (C8), 126.89 (C16), 126.16 and 126.11 (C4,7), 123.92 (C15),
122.80 (C17), 122.44 (C11), 121.17 00(C19), 120.84 (C9), 114.53 (C2),
Acknowledgements
0
000
0
00 000
68.30 (Ca ), 65.83 0 (Ca), 40.68 (Ca ), 40.29 (Ca ), 31.91(Ce,e ,e ,e ),
We would like to thank the Deutsche Forschungsgemeinschaft
for financial support (BO 1121/6-1)
0
00 000
00 00 000,d000
30.0e28.7 (Cb,d,b ,d ,b ,d ,b 00)0 , 27.45 and 27.12 (Cc ,c ), 25.93 and
0
0
00
0
00 000
26.02 (Cc,c ), 22.67 (Cf,f ,f ,f ), 14.08 (Cg,g ,g ,g ). Anal. Calcd for
C71H114N4O7: C 75.09, H 10.12, N 4.93. Found: C 75.36, H 10.35, N
4.93.
Supplementary data
1H and 13C NMR of compounds CA1e3, I1e3, and F1e3. Sup-
plementary data associated with this article can be found in the
data include MOL files and InChiKeys of the most important com-
pounds described in this article.
4.2.19. Intermediate I3.
References and notes
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2. Inata, H.; Matsumura, S. J. Appl. Polym. Sci. 1987, 34, 2609.
€
€
3. Leistner, D.; Stephan, M.; Haußler, L.; Vogel, R.; Ratzsch, M. Angew. Makromol.
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Int. 2003, 52, 1444.
Conversion of CA3 (2.900 g, 3.24 mmol) with 1-dodecanol
(1.208 g, 6.48 mmol). Dissolved in chloroform, precipitated with
acetone, yield: 66%. dH (CDCl3) 8.29 (2H, s, H11), 8.27 (2H, d, H80),
€
7. Maier, S.; Loontjens, T.; Scholtens, B.; Mulhaupt, R. Macromolecules 2003, 36, 4727.
€
8. Bohme, F.; Jakisch, L.; Komber, H.; Wursche, R. Polym. Degrad. Stab. 2007, 92, 2270.
€
€
9. Dung, B. T.; Jakisch, L.; Komber, H.; Haußler, L.; Voit, B.; Nghia, N. D.; Bohme, F.
Macromol. Chem. Phys. 2006, 207, 1953.
8.26 (4H, d, H3), 8.07 (2H, d, H9), 7.00 (4H, d, H2),0 4.38 (4H, t, Ha ),
€
10. Jakisch, L.; Komber, H.; Bohme, F. J. Polym. Sci. Polym. Chem. 2003, 41, 655.
0
4.05 (4H, t, Ha), 1.82 (8H, Hb,b ), 1.49 (8H, Hc,c ), 1.4e1.2 (40H,
€
11. Jakisch, L.; Komber, H.; Wursche, R.; Bohme, F. J. Appl. Polym. Sci. 2004, 94, 2170.
0
0
0
H
d,e,d ef ), 0.88 (6H, Hg ); dC (CDCl3) 165.12 (C13), 163.17 (C1), 159.08
12. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790.
13. Zeng, H. X.; Guan, Z. B. J. Am. Chem. Soc. 2011, 133, 1159.
(C6), 157.73 (C5), 147.41 (C12), 137.75 (C10), 130.41 (C3), 128.68 (C8),
128.25 (C11), 127.72 (C9), 121.89 (C4), 119.61 (C70), 114.67 (C20 ), 68.31
€
14. Jakisch, L.; Komber, H.; Bohme, F. Macromol. Mater. Eng. 2007, 292, 557.
€
€
15. Gube, A.; Jakisch, L.; Haußler, L.; Schneider, K.; Voit, B.; Bohme, F. Polym. Int.
0
0
(Ca), 66.01 (Ca ), 31.89 (Ce ), 30.0e29.0 (Cb,dee,d ), 28.63 (Cb ), 26.00
2012, 61, 157.
0
0
0
and 25.96 (Cc,c ), 22.65 (Cf ), 14.07 (Cg ). Anal. Calcd for
C64H84N2O10: C 73.82, H 8.13, N 2.69. Found: C 74.56, H 8.38, N
2.72.
16. Coppola, G. M. J. Heterocycl. Chem. 1999, 36, 563.
17. Donaruma, L. G.; Scelia, R. P.; Schonfeld, S. E. J. Heterocycl. Chem. 1964, 1, 48.
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