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0345826345
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Hernandulcin: Compadre, C. M.; Pezzuto, J. M.; Kinghorn, A. D.; Kamath, S. K. Science 1985, 227, 417.
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(b) Hernandulcin: Compadre, C. M.; Pezzuto, J. M.; Kinghorn, A. D.; Kamath, S. K. Science 1985, 227, 417.
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3
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37949005242
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Azadiradione: Lavie, D.; Levy, E. C.; Jain, M. K. Tetrahedron 1971, 27, 3927.
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(d) Azadiradione: Lavie, D.; Levy, E. C.; Jain, M. K. Tetrahedron 1971, 27, 3927.
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5
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0141495537
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Dichotenone A and B: Ali, M. S.; Pervez, M. K.; Saleem, M.; Ahmed, F. Nat. Prod. Res. 2003, 17, 301.
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Liotta, D.; Brown, D.; Hoekstra, W.; Monahan, R. III Tetrahedron Lett. 1987, 28, 1069.
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(a) Liotta, D.; Brown, D.; Hoekstra, W.; Monahan, R. III Tetrahedron Lett. 1987, 28, 1069.
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0030956932
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3, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249.
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3, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249.
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Leonard, N.M.1
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0037016958
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3, see: Répichet, S.; Zwick, A.; Vendier, L.; Le Roux, C.; Dubac, J. Tetrahedron Lett. 2002, 43, 993.
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33
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0037043188
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For exemples of the use of molecular sieves as acid scavenger, see: a
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For exemples of the use of molecular sieves as acid scavenger, see: (a) Vatèle, J.-M. Tetrahedron 2002, 58, 5689.
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Vatèle, J.-M.1
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Urata, H.1
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(c) Banks, A. R.; Fibiger, R. F.; Jones, T. J. Org. Chem. 1977, 42, 3965.
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33745669681
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7-induced 1,3-isomerization of allylic alcohols, see: (a) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2006, 128, 8142.
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7-induced 1,3-isomerization of allylic alcohols, see: (a) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2006, 128, 8142.
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39
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0036960331
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For other oxorhenium(VII) derivative catalyzed 1,3-allylic rearrangements of allylic alcohols, see: Bellemin-Laponnaz, S.; Le Ny, J. P. Compt. Rend. Chem. 2002, 5, 217.
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For other oxorhenium(VII) derivative catalyzed 1,3-allylic rearrangements of allylic alcohols, see: Bellemin-Laponnaz, S.; Le Ny, J. P. Compt. Rend. Chem. 2002, 5, 217.
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40
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48349142134
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General Procedure for Lewis Acid Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols with TEMPO and PhIO (Table 2) To a solution of tertiary alcohol (1 mmol) in CH2Cl2 (5 mL) were added PhIO (264 mg, 2 equiv) and TEMPO (15.6 mg, 0.1 equiv, For method B and C, powdered 4 Å MS was also added (0.08 and 0.13 g/mmol, respectively, The suspension was cooled to 0°C and Lewis acid was added. Dissolution of PhIO is indicative of the end of the reaction. For method A, just after dissolution of PhIO, powdered NaHCO3 was added and the stirring was continued for 10 min. In all cases, the reaction was poured onto a column of SiO2 (20 g) and eluted with EtOAc-PE 1:6, The purity of each synthesized carbonyl compound was checked by NMR spectroscopy
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2 (20 g) and eluted with EtOAc-PE (1:6). The purity of each synthesized carbonyl compound was checked by NMR spectroscopy.
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41
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35348824909
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For an overview of π-electrophilic Lewis acids, see
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For an overview of π-electrophilic Lewis acids, see: Yamamoto, Y. J. Org. Chem. 2007, 72, 7817.
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Yamamoto, Y.1
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42
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0029006202
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For a kinetic study of the oxidation of cyclohexanol and of its 2- and 3-methyl derivatives with TEMPO, see: de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Tetrahedron 1995, 51, 8023.
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For a kinetic study of the oxidation of cyclohexanol and of its 2- and 3-methyl derivatives with TEMPO, see: de Nooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Tetrahedron 1995, 51, 8023.
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43
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33745700261
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For an interesting comparative kinetic study of the oxidation of hindered secondary alcohols by TEMPO and 1-methyl-2-azaadamantane N-oxyl 1-Me-AZADO, a less hindered nitroxyl radical than TEMPO, see: Shibuya, M, Tomizawa, M, Suzuki, I, Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412
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For an interesting comparative kinetic study of the oxidation of hindered secondary alcohols by TEMPO and 1-methyl-2-azaadamantane N-oxyl (1-Me-AZADO), a less hindered nitroxyl radical than TEMPO, see: Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412.
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44
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0021962621
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For examples of activation of PhIO by acids, see: (a) Moriarty, R. M, Penmasta, R, Prakash, I. Tetrahedron Lett. 1985, 26, 4699
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For examples of activation of PhIO by acids, see: (a) Moriarty, R. M.; Penmasta, R.; Prakash, I. Tetrahedron Lett. 1985, 26, 4699.
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45
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0000208820
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(b) Zefirov, N. S.; Zhandkin, V. V.; Dan'kov, Y. V.; Sorokin, V. D.; Semerikov, V. N.; Koz'min, A. S.; Caple, R.; Berglund, B. A. Tetrahedron Lett. 1986, 27, 3971.
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Zefirov, N.S.1
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Sorokin, V.D.4
Semerikov, V.N.5
Koz'min, A.S.6
Caple, R.7
Berglund, B.A.8
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46
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0013613737
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(c) Lee, K.; Kim, D. Y.; Oh, D. Y. Tetrahedron Lett. 1988, 29, 667.
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Lee, K.1
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47
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0000814877
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(d) Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7195.
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Yang, Y.1
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Valentine, J.S.3
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48
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48349097779
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We have shown that allylic alcohols are rapidly oxidized, at 0°C, with TEMPO/PhIO/Yb(OTf)3 system, see ref. 6b
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3 system, see ref. 6b.
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51
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37049048425
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Bailey, N.; Carrington, A.; Lott, K. A. K.; Symons, M. C. R. J. Chem. Soc. 1960, 290.
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Symons, M.C.R.4
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52
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48349135573
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Strong protic acids are known to depolymerize PhIO, see ref. 17b.
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Strong protic acids are known to depolymerize PhIO, see ref. 17b.
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53
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48349137241
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4-catalyzed isomerization of allylic alcohols, see: (a) Narasaka, K.; Kusuma, H.; Hayashi, Y. Chem. Lett. 1991, 1413.
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4-catalyzed isomerization of allylic alcohols, see: (a) Narasaka, K.; Kusuma, H.; Hayashi, Y. Chem. Lett. 1991, 1413.
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54
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0026579169
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(b) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059.
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Narasaka, K.1
Kusama, H.2
Hayashi, Y.3
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55
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48349138198
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2. After 15 min, it was observed by TLC the disappearance of the starting material and formation of UV-absorbing, nonpolar products (dehydrated products).
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2. After 15 min, it was observed by TLC the disappearance of the starting material and formation of UV-absorbing, nonpolar products (dehydrated products).
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