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44949207941
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Examples:
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Examples:
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14
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Erman M.B., Aul'chenko I.S., Kheifits L.A., Dulova V.G., Novikov J.N., and Vol'pin M.E. Tetrahedron Lett. (1976) 2981-2984
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The Rupe rearrangement ( )
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The Rupe rearrangement (. Rupe H., and Kambli E. Helv. Chim. Acta 9 (1926) 672 )
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22
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44949103698
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{A figure is presented}
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{A figure is presented}
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23
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84955394357
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Yamamoto H. (Ed), Wiley-VCH, New York, NY
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In: Yamamoto H. (Ed). Lewis Acids in Organic Synthesis (2000), Wiley-VCH, New York, NY
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27
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26844516744
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For seminal examples illustrating this concept, see:
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For seminal examples illustrating this concept, see:. Georgy M., Boucard V., and Campagne J.-M. J. Am. Chem. Soc. 127 (2005) 14180-14181
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Georgy, M.1
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29
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44949212384
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Examples of Meyer-Schuster reactions of ethoxyalkynyl carbinols using hard Lewis or protic acids:
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Examples of Meyer-Schuster reactions of ethoxyalkynyl carbinols using hard Lewis or protic acids:
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31
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0017386028
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Welch S.C., Hagan C.P., White D.H., Fleming W.P., and Trotter J.W. J. Am. Chem. Soc. 99 (1977) 549-556
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33
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33746651540
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The combination of an electron-rich π-system and soft Lewis acid catalyst has also been used in cycloisomerization reactions:
-
The combination of an electron-rich π-system and soft Lewis acid catalyst has also been used in cycloisomerization reactions:. Sun J., Conley M.P., Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 128 (2006) 9705-9710
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Sun, J.1
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34
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44949123099
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Because the 1,3-hydroxy shift is not concerted and there is ample opportunity for the hydroxy to exchange with water in the reaction medium, the Meyer-Schuster reaction is not a true rearrangement. For mechanistic investigations of the Meyer-Schuster reaction, see:
-
Because the 1,3-hydroxy shift is not concerted and there is ample opportunity for the hydroxy to exchange with water in the reaction medium, the Meyer-Schuster reaction is not a true rearrangement. For mechanistic investigations of the Meyer-Schuster reaction, see:
-
-
-
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35
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0001484938
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Edens M., Boerner D., Chase C.R., Nass D., and Sciavelli M.D. J. Org. Chem. 42 (1977) 3403-3408
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39
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44949163405
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Recent examples: Refs. 15 and 19, and
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Recent examples: Refs. 15 and 19, and
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40
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32644449371
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49
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44949097750
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note
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The question as to what reaction pathway(s) leading from the propargyl acetate to the α,β-unsaturated ketone is catalyzed by cationic gold salts remains open. For further discussion, see Ref. 20f.
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50
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44949155873
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Related reactions of propargyl acetates:
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Related reactions of propargyl acetates:
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52
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34347246249
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Barluenga J., Riesgo L., Vincente R., Lopez L.A., and Tomas M. J. Am. Chem. Soc. 129 (2007) 7772-7773
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53
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38349014690
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Recent review on gold-catalyzed reactions of propargyl esters:
-
Recent review on gold-catalyzed reactions of propargyl esters:. Correa A., Marion N., Fensterbank L., Malacria M., Nolan S.P., and Cavallo L. Angew. Chem., Int. Ed. 47 (2008) 718-721
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Correa, A.1
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54
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44949126630
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For recent reviews, see Refs. 13 and 23 and:
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For recent reviews, see Refs. 13 and 23 and:
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59
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0000792433
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Yamamoto H. (Ed), Wiley-VCH, New York, NY Chapter 19
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Kobayashi S. In: Yamamoto H. (Ed). Sc(III) Lewis Acids. Lewis Acids in Organic Synthesis Vol. 2 (2000), Wiley-VCH, New York, NY 883-910 Chapter 19
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Kobayashi, S.1
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60
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34547213309
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For example, it was our inability to achieve Horner-Wadsworth-Emmons olefination reactions on either menthone (cf. 1h→3h) or menthone derivatives that initially prompted our interest in Meyer-Schuster reaction methodology. For more information on the steric congestion of menthone derivatives, see:
-
For example, it was our inability to achieve Horner-Wadsworth-Emmons olefination reactions on either menthone (cf. 1h→3h) or menthone derivatives that initially prompted our interest in Meyer-Schuster reaction methodology. For more information on the steric congestion of menthone derivatives, see:. Dudley G.B., Engel D.A., Ghiviriga I., Lam H., Poon K.W.C., and Singletary J.A. Org. Lett. 9 (2007) 2839-2842
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-
Dudley, G.B.1
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Lam, H.4
Poon, K.W.C.5
Singletary, J.A.6
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61
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44949150582
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note
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The Meyer-Schuster reactions of tertiary alcohols 2 may take a different course. Further investigations are planned and will be communicated in due course.
-
-
-
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62
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44949202051
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note
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Reactions conducted with less than a full equivalent of propanol were slow and inefficient, and are omitted from Table 5.
-
-
-
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64
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33644764723
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For full characterization, see:
-
For full characterization, see:. Zeitler K. Org. Lett. 8 (2006) 637-640
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(2006)
Org. Lett.
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Zeitler, K.1
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2942556883
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For full characterization, see:
-
For full characterization, see:. Imashiro R., and Seki M. J. Org. Chem. 69 (2004) 4216-4226
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(2004)
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Imashiro, R.1
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13144279278
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For full characterization, see:
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For full characterization, see:. Griaud L., Huber V., and Jenny T. Tetrahedron 54 (1998) 11899-11906
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(1998)
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Griaud, L.1
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67
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44949220651
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For full characterization, see:
-
For full characterization, see:
-
-
-
-
68
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0000062684
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Le Tadic-Biadatti M.-H., Callier-Dublanchet A.-C., Horner J.H., Quiclet-Sire B., Zard S.Z., and Newcomb M. J. Org. Chem. 62 (1997) 559-563
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Zard, S.Z.5
Newcomb, M.6
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