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(a) For a recent review on ynamides and ynamines, see: Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
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Viehe, H.G.1
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(e) Himbert, G. In Houben-Weyl, Methoden der organischen Chemie; Kropf, H.; Schaumann. E., Eds.; Georg Thieme Verlag: Stuttgart, 1993, 3267-3443.
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Himbert, G.1
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(e) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
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(c) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67.
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(a) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803.
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(b) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
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(a) Varela, J. A.; Castedo, L.; Saá, C. J. Am. Chem. Soc. 1998, 720, 12147.
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Mahía, J.4
Saá, C.5
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24
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1242347921
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As well as finding no precedent for the Glaser reaction of ynamides, we found only few ynamines dimerization: (a) Ficini, J.; Barbara, C.; d'Angelo, J. ; Duréault, A. Bull. Soc. Chim. Fr. 1974, 1535. (b) Mayerle, J. J.; Flandera, M. A. Acta Crystallogr., Section B 1978, 34, 1374; no experimental details are given.
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Ficini, J.1
Barbara, C.2
D'Angelo, J.3
Duréault, A.4
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25
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0000706251
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no experimental details are given
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As well as finding no precedent for the Glaser reaction of ynamides, we found only few ynamines dimerization: (a) Ficini, J.; Barbara, C.; d'Angelo, J. ; Duréault, A. Bull. Soc. Chim. Fr. 1974, 1535. (b) Mayerle, J. J.; Flandera, M. A. Acta Crystallogr., Section B 1978, 34, 1374; no experimental details are given.
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(1978)
Acta Crystallogr., Section B
, vol.34
, pp. 1374
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Mayerle, J.J.1
Flandera, M.A.2
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26
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0034604562
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For a recent review on acetylenic coupling, see: Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632.
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Angew. Chem. Int. Ed.
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Siemsen, P.1
Livingston, R.C.2
Diederich, F.3
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27
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1242280606
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note
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Trimethylsilyl derivatives are interesting substrates that can also be prepared in a single step from the corresponding N-alkyltosylamides by reaction with hypervalent iodonium reagents, see: ref. 5b
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29
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85085719087
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note
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3N gave a slow dimerization process.
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31
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1242280607
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note
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2: C, 66.65; H, 4.47; N, 5.18; S, 11.86. Found: C, 66.21; H, 4.21; N, 5.27; S, 11.67.
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32
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85085719419
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note
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3 before mixing with HCl (5%) or NaOH (10%).
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33
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0012483446
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Valenti, E.; Pericàs, M. A.; Serratosa, F. J. Am. Chem. Soc. 1990, 772, 7405.
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J. Am. Chem. Soc.
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Valenti, E.1
Pericàs, M.A.2
Serratosa, F.3
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34
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0002358128
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Ynamide 2b reacted much faster (in 0.5 h) than the non-nitrogenated acetylenes used by Mori and coworkers, which took 6-12 h. See: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Mori, A. ; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
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(1997)
Chem. Commun.
, pp. 1039
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Ikegashira, K.1
Nishihara, Y.2
Hirabayashi, K.3
Mori, A.4
Hiyama, T.5
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35
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0034708636
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Ynamide 2b reacted much faster (in 0.5 h) than the non-nitrogenated acetylenes used by Mori and coworkers, which took 6-12 h. See: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Mori, A. ; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
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(2000)
J. Org. Chem.
, vol.65
, pp. 1780
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Nishihara, Y.1
Ikegashira, K.2
Hirabayashi, K.3
Ando, J.-I.4
Mori, A.5
Hiyama, T.6
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