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35
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33847508513
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Use of TFA as an alternate catalyst was briefly examined. Reaction of 11 in pyrrole (64 mol equiv) catalyzed by TFA ( 1 mol equiv) also gave furylpyrromethane 15 in excellent yield (88%). However, reaction of 12 using TFA (1 mol equiv) gave 18 in 28% yield. More TFA (4 mol equiv) increased the yield to 76%.
-
Use of TFA as an alternate catalyst was briefly examined. Reaction of 11 in pyrrole (64 mol equiv) catalyzed by TFA ( 1 mol equiv) also gave furylpyrromethane 15 in excellent yield (88%). However, reaction of 12 using TFA (1 mol equiv) gave 18 in 28% yield. More TFA (4 mol equiv) increased the yield to 76%.
-
-
-
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36
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33847507657
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The furyl/thienylpyrromethane yields were insensitive to the excess of pyrrole over the range studied (23-66 mol equiv).
-
The furyl/thienylpyrromethane yields were insensitive to the excess of pyrrole over the range studied (23-66 mol equiv).
-
-
-
-
37
-
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33847513804
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Greater than 5-fold excesses of ethylmagnesium bromide and p-toluoyl chloride did not significantly increase the ratio of diacyldipyrromethane to monoacyldipyrromethane.
-
Greater than 5-fold excesses of ethylmagnesium bromide and p-toluoyl chloride did not significantly increase the ratio of diacyldipyrromethane to monoacyldipyrromethane.
-
-
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38
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33744602342
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note
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1H NMR spectroscopy of isolated samples. (Original NMR spectra of these byproducts are provided in the Supporting Information.)
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39
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0001583969
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Wallace, D. M.; Leung, S. H.; Senge, M. O.; Smith, K M. J. Org. Chem. 1993, 58, 7245-7257.
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41
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33744633666
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note
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3 in order to prevent rapid acidcatalyzed decomposition of the diols.
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-
-
-
42
-
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33744649230
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note
-
The signal-to-noise ratio of LD-MS typically exceeded 100:1. The MS method cannot exclude the selective scrambling yielding only the cis-porphyrin or the movement of the heteroatom within the core. However, rearrangement processes leading to such isomers would be expected to form a distribution of porphyrin products, including those of other masses. See ref 23.
-
-
-
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43
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33744674995
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note
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4Cl.
-
-
-
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44
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0001153211
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Srinivasan, N.; Hancy, C. A.; Lindsey, J. S.; Zhang, W.; Chait, B. T. J. Porphyrins Phihalocyanines 1999, 3, 283-291.
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0029680988
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0026315296
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