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M. Hoshi et al.
PAPER
(Z)-Tetradec-5-ene-7,9-diyne (8aa)
Eluent: pentane.
IR (neat): 2958, 2929, 2871, 2860, 1465, 731 cm–1.
1H NMR (500 MHz, CDCl3): d = 0.91 (t, J = 7.3 Hz, 3 H), 0.92 (t,
J = 7.3 Hz, 3 H), 1.30–1.47 (m, 6 H), 1.50–1.57 (m, 2 H), 2.30–2.36
(m, 4 H), 5.46 (d, J = 10.7 Hz, 1 H), 6.03 (dt, J = 10.7, 7.3 Hz, 1 H).
13C NMR (125 MHz, CDCl3): d = 13.5 (CH3), 13.9 (CH3), 19.3
(CH2), 21.9 (CH2), 22.2 (CH2), 30.3 (CH2), 30.4 (CH2), 30.9 (CH2),
65.1 (≡C), 72.0 (≡C), 78.1 (≡C), 84.8 (≡C), 108.1 (=CH), 147.7
(=CH).
2005, 61, 1903. (h) Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org.
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771. (k) Zhu, B. C.; Jiang, X. Z. Appl. Organomet. Chem.
2007, 21, 345. (l) Yan, J.; Lin, F.; Yang, Z. Synthesis 2007,
1301. (m) Yan, F.; Cui, X.; Li, Y.-N.; Zhang, J.; Ren, G.-R.;
Wu, Y. Tetrahedron 2007, 63, 1963. (n) Kurita, T.; Abe,
M.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Synlett 2007,
2521. (o) Yan, J.; Wu, J.; Jin, H. J. Organomet. Chem. 2007,
692, 3636. (p) Kamata, K.; Yamaguchi, S.; Kotani, M.;
Yamaguchi, K.; Mizuno, N. Angew. Chem. Int. Ed. 2008, 47,
2407. (q) Li, D.; Yin, K.; Li, J.; Jia, X. Tetrahedron Lett.
2008, 49, 5918. (r) Chen, S.-N.; Wu, W.-Y.; Tsai, F.-Y.
Green Chem. 2009, 11, 269. (s) Kuhn, P.; Alix, A.;
Kumarraja, M.; Louis, B.; Pale, P.; Sommer, J. Eur. J. Org.
Chem. 2009, 423. (t) Hilt, G.; Hengst, C.; Arndt, M.
Synthesis 2009, 395. (u) Li, L.; Wang, J.; Zhang, G.; Liu, Q.
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T.; Yamaguchi, K.; Mizuno, N. Chem. Eur. J. 2009, 15,
7539. (w) Adimurthy, S.; Malakar, C. C.; Beifuss, U. J. Org.
Chem. 2009, 74, 5648. (x) Chassaaing, S.; Alix, A.;
Boningari, T.; Sani Souna Sido, K.; Keller, M.; Kuhn, P.;
Louis, B.; Sommer, J.; Pale, P. Synthesis 2010, 1557.
(y) Balaraman, K.; Kesavan, V. Synthesis 2010, 3461.
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2003, 68, 7085. (b) Chen, Z.; Jiang, H.; Wang, A.; Yang, S.
J. Org. Chem. 2010, 75, 6700.
HRMS (EI): m/z [M+] calcd for C14H20: 188.1565; found: 188.1559.
(Z)-1-Phenyldec-5-ene-1,3-diyne (8ab)
Eluent: pentane–CH2Cl2 (9:1).
IR (neat): 3020, 2956, 2927, 2858, 1488, 1463, 1442, 1398, 1026,
914, 754, 732, 688 cm–1.
1H NMR (500 MHz, CDCl3): d = 0.92 (t, J = 7.3 Hz, 3 H), 1.32–
1.45 (m, 4 H), 2.34–2.41 (m, 2 H), 5.56 (d, J = 10.7 Hz, 1 H), 6.09
(dt, J = 10.7, 7.3 Hz, 1 H), 7.27–7.37 (m, 3 H), 7.46–7.51 (m, 2 H).
13C NMR (125 MHz, CDCl3): d = 13.9 (CH3), 22.2 (CH2), 30.6
(CH2), 30.9 (CH2), 74.1 (≡C), 77.6 (≡C), 79.0 (≡C), 81.6 (≡C),
107.9 (=CH), 121.9 (Carom), 128.3 (2 × CHarom), 129.0 (CHarom),
132.3 (2 × CHarom), 148.6 (=CH).
HRMS (EI): m/z [M+] calcd for C16H16: 208.1252; found: 208.1245.
(7) (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.;
Hiyama, T. Chem. Commun. 1997, 1039. (b) Ishikawa, T.;
Ogawa, A.; Hirao, T. Organometallics 1998, 17, 5713.
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Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
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5511. (e) Shirakawa, E.; Nakao, Y.; Murota, Y.; Hiyama, T.
J. Organomet. Chem. 2003, 670, 132. (f) Yoshida, H.;
Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003,
1510. (g) Oh, C. H.; Reddy, V. R. Tetrahedron Lett. 2004,
45, 5221. (h) Nishihara, Y.; Okamoto, M.; Inoue, Y.;
Miyazaki, M.; Miyasaka, M.; Takagi, K. Tetrahedron Lett.
2005, 46, 8661. (i) Krasovskiy, A.; Tishkov, A.; del Amo,
V.; Mayr, H.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45,
5010. (j) Cahiez, G.; Moyeux, A.; Buendia, J.; Duplais, C.
J. Am. Chem. Soc. 2007, 129, 13788. (k) Paixão, M. W.;
Weber, M.; Braga, A. L.; de Azeredo, J. B.; Deobald, A. M.;
Stefani, H. A. Tetrahedron Lett. 2008, 49, 2366. (l) Maji,
M. S.; Pfeifer, T.; Studer, A. Angew. Chem. Int. Ed. 2008,
47, 9547. (m) Singh, F. V.; Amaral, M. F. Z. J.; Stefani, H.
A. Tetrahedron Lett. 2009, 50, 2636.
(Z)-1-Phenyldec-1-ene-3,5-diyne (8ba)
Eluent: pentane–CH2Cl2 (9:1).
IR (neat): 2958, 2931, 2871, 2225, 1492, 1448, 781, 690 cm–1.
1H NMR (500 MHz, CDCl3): d = 0.92 (t, J = 7.3 Hz, 3 H), 1.39–
1.48 (m, 2 H), 1.50–1.59 (m, 2 H), 2.37 (t, J = 7.3 Hz, 2 H), 5.71
(dd, J = 12.2, 1.0 Hz, 1 H), 6.70 (d, J = 12.2 Hz, 1 H), 7.34–7.49 (m,
3 H), 7.77–7.85 (m, 2 H).
13C NMR (125 MHz, CDCl3): d = 13.5 (CH3), 19.4 (CH2), 21.9
(CH2), 30.2 (CH2), 65.3 (≡C), 73.2 (≡C), 81.1 (≡C), 86.9 (≡C),
106.2 (=CH), 128.3 (2 × CHarom), 128.4 (2 × CHarom), 128.9
(CHarom), 136.1 (Carom), 141.6 (=CH).
HRMS (EI): m/z [M+] calcd for C16H16: 208.1252; found: 208.1253.
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Synthesis 2011, No. 23, 3839–3847 © Thieme Stuttgart · New York