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0344327788
-
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note
-
The reaction with a secondary benzylic alcohol, 1-phenylethanol, as an alkylating agent gave styrene as a major product, and several unidentified products were also formed. See ref 10b.
-
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47
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0032917310
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48
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0344327786
-
-
note
-
2a is suitable as a nucleophile for investigating the reactivity of the generated cation, since 2a is selectively alkylated at the 4 position on the naphthalene ring, and unalkylated 2a is recovered without decomposition and is easy to detect by UV absorption. The selective alkylation is due to the electron-withdrawing ester group; therefore, 2a is less nucleophilic than an electron-rich aromatic compound, such as anisole or furan (Chart 1).
-
-
-
-
50
-
-
0000604190
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0002000859
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For a review of Lewis acid-promoted enolate alkylations, see: Reetz, M. T. Angew. Chem., Int. Ed. Eng. 1982, 21, 96-108.
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Reetz, M.T.1
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53
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0345190225
-
-
note
-
3-(2-Naphthyl)-1-phenyl-1-butene.
-
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-
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54
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-
0344759841
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0000386465
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-
56
-
-
0344327787
-
-
note
-
4-catalyzed reaction.
-
-
-
-
57
-
-
0345190224
-
-
note
-
endo-Olefin: 1-methyl-3,4-dihydronaphthalene.exo-Olefin: 1-methylene-1,2,3,4-tetrahydro-naphthalene.
-
-
-
-
59
-
-
0000059738
-
-
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60
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0018425810
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61
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63
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0000510466
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(a) Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem. 1998, 63, 7505-7515.
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0015239868
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Johnson, W. S.; Gravestock, M. B.; McCarry, B. E. J. Am. Chem. Soc. 1971, 93, 4332-4334.
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-
67
-
-
0345190222
-
-
note
-
The yields of 30 and 31 were calculated based on 20.
-
-
-
-
68
-
-
0345622412
-
-
note
-
The yields were calculated based on 37.
-
-
-
-
69
-
-
0345190223
-
-
note
-
For the reaction with 1, 2-vinylnaphthalene was formed, and for the reaction with 4a, styrene was formed. The structures of the byproducts derived from these olefins are shown in Figure 4.
-
-
-
-
70
-
-
0032547286
-
-
Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287-8288.
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Kobayashi, S.1
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