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For examples of regioisomeric mixtures of products obtained from the use of terminal alkynes in the Trofimov reaction see
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See also ref 24.
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For the base-mediated synthesis of benzophenone-derived O -vinyl oximes from alkynes, see: Zaitsev, A. B.; Vasil'tsov, A. M.; Schmidt, E. Y.; Mikhaleva, A. I.; Morozova, L. V.; Afonin, A. V.; Ushakov, I. A.; Trofimov, B. A. Tetrahedron 2002, 58, 10043
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107
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0343090371
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For the base-mediated synthesis of O -vinyl oximes with enolizable oximes, see: Trofimov, B. A.; Mikhaleva, A. I.; Vasil'tsov, A. M.; Schmidt, E. Y.; Tarasova, O. A.; Morozova, L. V.; Sobenina, L. N.; Preiss, T.; Henkelmann, J. Synthesis 2000, 1125
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79955560419
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1H NOESY experiments were used for further verification.
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1H NOESY experiments were used for further verification.
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109
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79955570323
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Compounds 3d, 3e, 3f, and 3i were reported in our previous communication. See ref 24.
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Compounds 3d, 3e, 3f, and 3i were reported in our previous communication. See ref 24.
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79955556480
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These substrates gave low yields or no conversion when run under the same reaction conditions at 25 °C.
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These substrates gave low yields or no conversion when run under the same reaction conditions at 25 °C.
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111
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0000553208
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For examples of cascade processes involving the Stetter reaction or oxidative enolate coupling with the Paal-Knorr reaction, see: Szakal-Quin, G.; Graham, D. G.; Millington, D. S.; Maltby, D. A.; McPhail, A. T. J. Org. Chem. 1986, 51, 621
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79955557022
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The regiochemistry of pyrroles 4a, 4b, and 4m-v was misrepresented in our previous communication. (24)
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The regiochemistry of pyrroles 4a, 4b, and 4m-v was misrepresented in our previous communication. (24)
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79955562790
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Less than 5% of 2 and the corresponding ketone were isolated with the pyrrole products. The remainder of the starting material is most likely converted into a highly colored polymeric material which remains physisorbed to silica gel.
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Less than 5% of 2 and the corresponding ketone were isolated with the pyrrole products. The remainder of the starting material is most likely converted into a highly colored polymeric material which remains physisorbed to silica gel.
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118
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79955563373
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The proposed mechanism for 3-cyano-4-methylpyrrole formation is based on analogous mechanisms determined and proposed for the Fisher indole and Trofimov reactions. See refs 15f, 20c, and 20d.
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The proposed mechanism for 3-cyano-4-methylpyrrole formation is based on analogous mechanisms determined and proposed for the Fisher indole and Trofimov reactions. See refs 15f, 20c, and 20d.
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Attempts at isolation of 5s by silica gel chromatography led to the isolation of 4s.
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Attempts at isolation of 5s by silica gel chromatography led to the isolation of 4s.
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Solvent choice showed little effect on the base-promoted rearrangement and cyclization of 2b to 3b.
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Solvent choice showed little effect on the base-promoted rearrangement and cyclization of 2b to 3b.
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79955552529
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See the Supporting Information for a comparison of NMR data to literature values.
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See the Supporting Information for a comparison of NMR data to literature values.
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