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2742550402
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note
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2 at room temperature provided N,N-diethyl-4-iodoaniline (92%), exclusively. A similar treatment afforded 4-iodoaniline (0.5/1, 15min, 68%), 4-iodo-N-methylaniline (1/1, 1h, 75%) and 4-iodoacetanilide (3/3, 17h, 72%).
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34
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note
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The solution may be washed with a hypo solution to remove excess iodine.
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37
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0001307168
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Interestingly, under these conditions benzofuran was recovered unchanged, and benzo[b]thiophene was converted to its 3-iodo derivative. See: R. Gaertner, J. Am. Chem. Soc. 74, 4950 (1952)
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40
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2742526270
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note
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Six- and seven-membered benzocyclic amides, such as N-acetyl-1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H/-benzazepin-2-one, were found to be unreactive.
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