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Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chap. 10
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29044432919
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Tri-tert-butylpyrimidine (TTBP) and 2,6-di-tert-butyl-4-methylpyridine (2,6-DTBMP) were equally effective in this role.
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85005617766
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The E-stereochemical outcome of this side-reaction is in accord with mechanistic studies on this type of E' elimination: (a) Matassa, V. G.; Jenkins, P. R.; Kümin, A.; Damm, L.; Schreiber, J.; Felix, D.; Zass, E.; Eschenmoser, A. Isr. J. Chem. 1989, 29, 321.
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(c) Archibald, S. C.; Barden, D. J.; Bazin, J. F. Y.; Fleming, I.; Foster, C. F.; Mandal, A. K.; Mandal, A. K.; Parker, D.; Takaki, K.; Ware, A. C.; Williams, A. R. B.; Zwicky, A. B. Org. Biomol. Chem. 2004, 2, 1051.
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Pornet, J.1
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29044438372
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The silyl tether is part of a vinylsilane in this intermediate and will be less effective in stabilising the β-vinyl carbocation on geometric grounds.
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22
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4644241208
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For some recent examples of propargylsilanes in synthesis: (a) Patel, P. P.; Zhu, Y.; Zhang, L.; Herndon, J. W. J. Organomet. Chem. 2004, 689, 3379.
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For recent examples where propargylsilanes have been employed in intramolecular reactions: (a) Shin, C.; Chavre, S. N.; Pae, A. N.; Cha, J. H.; Koh, H. Y.; Chang, M. H.; Choi, J. H.; Cho, Y. S. Org. Lett. 2005, 7, 3283.
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29044442781
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Propargyltrimethylsilane is commercially available although expensive and invariably contaminated with varying amounts of allenyltrimethylsilane. We find it more convenient to prepare the reagent ourselves.
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