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0345557144
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note
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Treatment of piperonyl alcohol (152 mg, 1 mmol) with boiling MeOH (150 ml) for 3 h in the presence of 10% Pd-C (186 mg) did not afford the methyl ether, but produced piperonal (120 mg, 80%). Accordingly, this procedure appears to be ineffective for benzylation of alcohols.
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25
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0344694942
-
-
note
-
EtOH nm (ε): 250 (23700), 285 (sh) (7300), 306 (10500).
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28
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0344694941
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0344263219
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-
note
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3) δ: 3.99 (3H, s, Me), 5.71 (2H, s, CH2), 7.20 [1H, d, J=1.7 Hz, C(6)-H], 7.50 [2H, m, C(2′)-, C(6′)-H], 7.63 [1H, d, J=1.7 Hz, C(7)-H], 7.83 [1H, s, C(2)-H], 8.22 [2H, m, C(3′)-, C(5′)-H].
-
-
-
-
31
-
-
0344263220
-
-
note
-
3) δ: 4.01 (3H, s, Me), 6.04 (2H, s, CH2), 7.20 [1H, d, J=1.7 Hz, C(6)-H], 7.48-7.68 [2H, m, C(5′)-, C(6′)-H], 7.63 [1H, d, J= 1.7 Hz, C(7)-H], 7.91 [1H, s,C(2)-H], 8.13-8.23 [1H, m, C(3′)-H].
-
-
-
-
32
-
-
0345125626
-
-
note
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30)
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-
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34
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84987318534
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0344263193
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0344263192
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47
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0000276890
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b) Activation of carbonyl groups by an intramolecular hydroxy group through hydrogen bonding has also been reported for allylation of carbonyl compounds: Yasuda M., Fujibayashi T., Baba A., J. Org. Chem., 63, 6401-6404 (1998); Ito H., Ujita Y., Tateiwa J., Sonoda M., Hosomi A., Chem. Commun., 1998, 2443-2444.
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85046499979
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b) Activation of carbonyl groups by an intramolecular hydroxy group through hydrogen bonding has also been reported for allylation of carbonyl compounds: Yasuda M., Fujibayashi T., Baba A., J. Org. Chem., 63, 6401-6404 (1998); Ito H., Ujita Y., Tateiwa J., Sonoda M., Hosomi A., Chem. Commun., 1998, 2443-2444.
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50
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0344694923
-
-
note
-
-1: 1682 (CO).
-
-
-
-
51
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-
0029964665
-
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Assigned by comparison of the peak height of this signal with that of the other CH signal: Itaya T., Ito N., Fujii T., Chem. Pharm. Bull., 44, 594-598 (1996).
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Itaya, T.1
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52
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0345125601
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For example, see Bunnett J. F., "Investigation of Rates and Mechanisms of Reactions," 3rd ed., Part I, ed. by Lewis E. S., John Wiley and Sons, New York, 1974, pp. 145-153.
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Bunnett, J.F.1
|