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84874217580
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It is reported that deacetylation of propargylic tertiary acetates is exceptionally high as compared with other tertiary acetates
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It is reported that deacetylation of propargylic tertiary acetates is exceptionally high as compared with other tertiary acetates.
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31
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41349089895
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A. Sniady, A. Durham, M. S. Morreale, A. Marcinek, S. Szafert, T. Lis, K. R. Brzezinska, T. Iwasaki, T. Ohshima, K. Mashima, R. Dembinski, J. Org. Chem. 2008, 73, 5881.
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34
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84874204628
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The Zn cluster 1 is marketed as ZnTAC24 from STREM produced by Takasago International corp., Japan
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The Zn cluster 1 is marketed as ZnTAC24 from STREM (produced by Takasago International corp., Japan).
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35
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0025186348
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a) S. K. Burley, P. R. David, A. Taylor, W. N. Lipscomb, Proc. Natl. Acad. Sci. USA 1990, 87, 6878;
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17444395097
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For a general review, see: a, Eds.: M. Shibasaki, Y Yamamoto, Wiley-VCH, Weinheim, for representative examples of multinuclear zinc catalysts, see
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For a general review, see: a) Multimetallic Catalysts in Organic Synthesis (Eds.: M. Shibasaki, Y Yamamoto), Wiley-VCH, Weinheim, 2004; for representative examples of multinuclear zinc catalysts, see
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Multimetallic Catalysts in Organic Synthesis
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40
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0034801857
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N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466;
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B. M. Trost, H. Ito, E. R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367.
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Trost, B.M.1
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42
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84874214044
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Although both MeOH and EtOH gave nearly the same results, we set MeOH rather than EtOH as the standard nucleophile because of larger boiling temperature difference between nucleophile and coproduct ester MeOH: 64.5°C, MeOAc: 57-58°C, DT ≈ 7°C; EtOH: 78.3°C, EtOAc: 77.1 °C, ΔT=1.2°C
-
Although both MeOH and EtOH gave nearly the same results, we set MeOH rather than EtOH as the standard nucleophile because of larger boiling temperature difference between nucleophile and coproduct ester (MeOH: 64.5°C, MeOAc: 57-58°C, DT ≈ 7°C; EtOH: 78.3°C, EtOAc: 77.1 °C, ΔT=1.2°C).
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45
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84874212615
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18 the Zn cluster showed comparable catalyst activity in various solvents, including hexane, toluene, chlorobenzene, diglyme, dioxane, DMF, and DMSO. Thus, in the case of substrates that are insoluble in alcohols, mix-solvent system would be a good choice of solvents. For example, the deacetylation of 2a 1.0 mmol in MeOH/hexane 1:1, 2 mL gave 3a in 89% yield
-
[18] the Zn cluster showed comparable catalyst activity in various solvents, including hexane, toluene, chlorobenzene, diglyme, dioxane, DMF, and DMSO. Thus, in the case of substrates that are insoluble in alcohols, mix-solvent system would be a good choice of solvents. For example, the deacetylation of 2a (1.0 mmol) in MeOH/hexane (1:1, 2 mL) gave 3a in 89% yield.
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46
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84874214741
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10c, 14
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[10c, 14]
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-
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47
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0000894377
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For a review, see
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For a review, see: S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429.
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Swaminathan, S.1
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|