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34047237359
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For better readability, the generic name pyridones is used in this article, the case of pyridone 1a, rapid prototropy induces the formation of the more stable
-
For better readability, the generic name pyridones is used in this article. In the case of pyridone 1a, rapid prototropy induces the formation of the more stable 6-hydroxypyridine-3-carboxylate 3a.
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6-hydroxypyridine-3-carboxylate
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34047201467
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2O, MeOH, DMF, MeCN, AcOEt, and THF were used, without yielding any improvement.
-
2O, MeOH, DMF, MeCN, AcOEt, and THF were used, without yielding any improvement.
-
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29
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34047238985
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The transfer of the sulfonyl group from nitrogen to oxygen is probably disfavored under hyperbaric conditions. See ref 9 for various discussions on this type of process
-
The transfer of the sulfonyl group from nitrogen to oxygen is probably disfavored under hyperbaric conditions. See ref 9 for various discussions on this type of process.
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30
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0000164230
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Biactivation by Lewis acids and high pressures has been reported to induce higher yields and selectivities. See: (a) Revial, G, Blanchard, M, d'Angelo, J. Tetrahedron Lett. 1983, 24, 899-902
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Biactivation by Lewis acids and high pressures has been reported to induce higher yields and selectivities. See: (a) Revial, G.; Blanchard, M.; d'Angelo, J. Tetrahedron Lett. 1983, 24, 899-902.
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0022523094
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Interaction between the diene and the dienophile occurred exclusively from the less hindered, convex face of the latter; there are precedents in the literature for such behavior. See, for instance: (a) Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908-5919.
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Interaction between the diene and the dienophile occurred exclusively from the less hindered, convex face of the latter; there are precedents in the literature for such behavior. See, for instance: (a) Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908-5919.
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46
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34047192728
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Endo addition can be defined as that particular spatial arrangement of reactants in which the more bulky side of the diene is under the more bulky side of the dienophile, meaning the pyridone cycle in this case. See: Fringuelli, F.; Taticchi, A. In Dienes in the Diels-Alder Reaction; John Wiley and Sons Ltd.: New York, 1990; pp 1-44.
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Endo addition can be defined as "that particular spatial arrangement of reactants in which the more bulky side of the diene is under the more bulky side of the dienophile", meaning the pyridone cycle in this case. See: Fringuelli, F.; Taticchi, A. In Dienes in the Diels-Alder Reaction; John Wiley and Sons Ltd.: New York, 1990; pp 1-44.
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47
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34047210386
-
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Hydrolysis of the silyl enol ethers was carried out by stirring a methylene chloride solution of the subtrate in the presence of silica; see Experimental Section
-
Hydrolysis of the silyl enol ethers was carried out by stirring a methylene chloride solution of the subtrate in the presence of silica; see Experimental Section.
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54
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34047216382
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Only dimerization of cyclopentadiene could be observed
-
Only dimerization of cyclopentadiene could be observed.
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4 catalysis, have been shown to yield inverse-electron-demand [4 + 2] heterocycloadducts, rather than normal-electron-demand [4 + 2] products. See: Denmark, S. E.; Kesley, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912-4924.
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4 catalysis, have been shown to yield inverse-electron-demand [4 + 2] heterocycloadducts, rather than normal-electron-demand [4 + 2] products. See: Denmark, S. E.; Kesley, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912-4924.
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34047240852
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Molecular model inspection shows that the two double bonds in 12d-f are closer than those in 12a-c. Hence, the [3,3] sigmatropic rearrangement should be more favored from the IED cycloadducts obtained from cyclopentadiene, if the equilibrium is shifted towards the formation of the NED adducts
-
Molecular model inspection shows that the two double bonds in 12d-f are closer than those in 12a-c. Hence, the [3,3] sigmatropic rearrangement should be more favored from the IED cycloadducts obtained from cyclopentadiene, if the equilibrium is shifted towards the formation of the NED adducts
-
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62
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34047239258
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It has to be kept in mind, however, that, in this precise case, an endo approach involving the s-trans conformer of dimethylbutadiene 4a would also allow stabilization of the secondary orbital interactions to take place, but would suffer from steric hindrance generated by the methyl groups as well. Such an approach would only give rise to IED endo cycloadduct 12a, and thus to the observed biscycloadduct 14a. Diagram presented
-
It has to be kept in mind, however, that, in this precise case, an endo approach involving the s-trans conformer of dimethylbutadiene 4a would also allow stabilization of the secondary orbital interactions to take place, but would suffer from steric hindrance generated by the methyl groups as well. Such an approach would only give rise to IED endo cycloadduct 12a, and thus to the observed biscycloadduct 14a. Diagram presented
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