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16
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0030592681
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(a) Klötgen, S.; Fröhlich, R.; Würthwein, E.-U. Tetrahedron 1996, 52, 14801.
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Tetrahedron
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Klötgen, S.1
Fröhlich, R.2
Würthwein, E.-U.3
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20
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35648954670
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Preparation of 1-[2-(Hex-1-ynyl)benzylidene]-2-phenylhydrazine (12a, A mixture of 2-(1-hexynyl)benz-aldehyde (0.93 g, 5.00 mmol) and phenylhydrazine (0.54 g, 5.00 mmol) in anhyd CH2Cl2 (20 mL) was stirred in the presence of molecular sieves (4 Å) at r.t. for 16 h. Molecular sieves were removed by filtration through Celite and washed with CH2Cl2 (20 mL, The solvent was removed in vacuo to afford the hydrazone 12a (1.10 g, 4.00 mmol, 80, as a yellow oil. The obtained hydrazone was pure enough to be used without further purification. FTIR (film, 3313 (br, w, 2931 (s, 2871 (s, 2862 (m, 2225 (m, 1575 (m, 1494 (s, 1448 (m, 1257 (s, 1145 (m) cm-1. 1H NMR (400 MHz, CDCl 3, δ, 0.98 (t, J, 7.3 Hz, 3 H, 1.47-1.68 (m, 4 H, 2.48 (t, J, 7.4 Hz, 2 H, 6.87 (tt, J, 7.3, 1.2 Hz, 1 H, 7.11-7.14 (m, 2 H, 7.19 (dd, J, 7.4, 1.4 Hz, 1 H, 7.25-7.30 m, 3 H
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2: C, 82.57; H, 7.29; N, 10.14. Found: C, 82.87; H, 7.48; N, 9.57.
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21
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35649009960
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Preparation of 1-(2-Butyl-1H-inden-1-ylidene)-2- phenylhydrazine (13a, Hydrazone 12a (0.28 g, 1.00 mmol) was added under argon to the solution of t-BuOK (0.22 g, 2.00 mmol) in DMF (5 mL) and the mixture was stirred at 50°C until all starting hydrazone had disappeared (approx. 5 h, TLC monitoring, H2O (20 mL) was added and the mixture was extracted with Et2O (3 x 20 mL, The combined organic extracts were dried with MgSO4 and the residue was purified by flash chromatography (Et2O-pentane-Et3N, 0.5:10:0.2) giving 13a (0.07 g, 0.25 mmol, 25, as a yellowish oil. FTIR (film, 2956 (s, 2927 (s, 1600 (s, 1566 (s, 1504 (s, 1494 (s, 1255 (s, 1207 (s, 1168 (s, 1151 (w, 1122 (m, 1093 (w) cm-1. 1H NMR (500 MHz, CDCl3, δ, 1.00 (t, J, 7.1 Hz, 3 H, 1.43-1.52 (m, 2 H, 1.68-1.75 (m, 2 H, 2.66-2.69 (m, 2 H, 6.56 (s, 1 H, 7.03 tt, J
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2: C, 82.57; H, 7.29; N, 10.14. Found: C, 82.64; H, 7.54; N, 9.62.
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22
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35648950547
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2(OH). 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, E-mail: deposit@ccdc.cam.ac.uk].
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2(OH). 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, E-mail: deposit@ccdc.cam.ac.uk].
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35649010457
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4 and the residue was purified by flash chromatography (tert-butyl methyl ether) giving 15 (0.09 g, 0.47 mmol, 47%) as a yellow oil. All spectroscopic and physical data were in accordance with published data (see ref. 11).
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4 and the residue was purified by flash chromatography (tert-butyl methyl ether) giving 15 (0.09 g, 0.47 mmol, 47%) as a yellow oil. All spectroscopic and physical data were in accordance with published data (see ref. 11).
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26
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Bast, K.; Behrens, M.; Durst, T.; Gashey, R.; Huisgen, R.; Schiffer, R.; Temme, R. Eur. J. Org. Chem. 1998, 379.
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Bast, K.1
Behrens, M.2
Durst, T.3
Gashey, R.4
Huisgen, R.5
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Temme, R.7
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27
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Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A. Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith
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(a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
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Details of the quantum chemical calculations may be obtained from E.-U. Würthwein upon request
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(b) Details of the quantum chemical calculations may be obtained from E.-U. Würthwein upon request.
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