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15944414407
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note
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(a) 2-Iodoaniline 8a is commercially available. The substituted 2-iodoanilines 8b, 8c and 8e were prepared from the commercially available 4-methylaniline, 2-nitro-4-methoxyaniline and 4-fluoroaniline, respectively, according to the procedure described by Ma et al.12b Ethyl 4-amino-3- iodobenzoate 8d and 4-nitro-2-iodoaniline 8f were prepared from commercially available ethyl 4-aminobenzoate and 4-nitroaniline, respectively by iodination according to the procedure described by Spivey et al. and Adimurthy et al., respectively.12c,d
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32
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0035967767
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36
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15944420394
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note
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3N as base and an equimolar amount of copper and palladium catalysts (0.01 equiv). Iododerivatives 9d and 9f show low solubility in THF and a mixture of THF-DMF was used as solvent.
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37
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15944376744
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note
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3 was adjusted depending on the solubility of the starting aldehydes. The above-mentioned reaction proceeds slowly at r.t. (typically 2 d). Notably, worse results have been obtained by heating the reaction mixture.
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39
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0000035972
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(a) Only E-isomers of acids 13 were obtained (NMR analysis). The Wittig reaction of ylide 12 with the aldehydes affords the 3-(E)-alkylidene-succinic acid monoalkyl esters in a highly stereoselective way; for previous studies on this reaction see: Paquette, L. A.; Schulze, M. M.; Bolin, D. J. Org. Chem. 1994, 59, 2043.
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Schulze, M.M.2
Bolin, D.3
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41
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15944412340
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note
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+], 427, 382, 354, 334, 315, 290, 272, 244, 227, 200, 171, 155, 139, 120, 91, 65.
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