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After a report of our preliminary results,9a Decreay and Collman published the observation of corrole formation in modest yield from a dipyrromethanedicarbinol + 2,2′-bipyrrole route.9b In a recent review article on corrole synthesis,9c Gryko reported that his group has also attempted to prepare meso-substituted corrole via 2,2′-bipyrrole but without success. To the best of our knowledge, the details of their work have not been published. (a) Geier, G. R., III; Grindrod, S. C.; Callinan, J. B.; Reid, C. G. Abstr. Papers Am. Chem. Soc. 2002, 224, 750.
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(b) Geier, G. R., III; Littler, B. J.; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 712-718.
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note
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Although 2,2′-bipyrrole is now commercially available (Alfa Aesar), its relatively high price (1 g, $224) provided the impetus to further improve its synthesis.
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33
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0029632229
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Groenendaal, L.; Peerlings, H. W. I.; van Dongen, J. L. J.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Macromolecules 1995, 28, 116-123.
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Havinga, E.E.4
Vekemans, J.A.J.M.5
Meijer, E.W.6
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34
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4644281598
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note
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We considered the possibility that DDQ might interfere with the detection of HPO as we had observed to be the case in our previous studies involving the synthesis of TPC.11 Thus, samples were washed with an aqueous basic dithionite solution prior to analysis by TLC and UV-vis.
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35
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4644317192
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note
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As it turned out, TPC was rarely produced in reactions of 1a-OH with 3 according to TLC analysis; thus, it was not typically necessary to determine the yield of TPC in the presence of HPO.
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36
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0034602310
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Rao, P. D.; Dhanalekshmi, S.; Littler, B. J.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7323-7344.
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Rao, P.D.1
Dhanalekshmi, S.2
Littler, B.J.3
Lindsey, J.S.4
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37
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4644229810
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note
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2 required brief sonication in order to produce a solution of bipyrrole that was not visibly light scattering.
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38
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4644273837
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note
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The quantity of acid is reported in concentration units of molarity for convenience of comparison of reaction conditions; however, these four acids are poorly soluble and the reaction mixtures were generally heterogeneous as reported previously.12
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39
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0033574515
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Littler, B. J.; Ciringh, Y.; Lindsey, J. S. J. Org. Chem. 1999, 64, 2864-2872.
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Littler, B.J.1
Ciringh, Y.2
Lindsey, J.S.3
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0035528864
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Geier, G. R., III; Littler, B. J.; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 701-711.
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J. Chem. Soc., Perkin Trans. 2
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Geier III, G.R.1
Littler, B.J.2
Lindsey, J.S.3
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42
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4644336708
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note
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2 was used to elute HpFPO from the silica pad.
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43
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4644294040
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note
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We did not attempt to use p-chloranil because DDQ did not appear to interfere with the isolation of HpFPO, and we had previously encountered difficulties when attempting to use p-chloranil in the synthesis of TpFPC.
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0034649139
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Ka, J.-W.; Cho, W.-S.; Lee, C.-H. Tetrahedron Lett. 2000, 41, 8121-8125.
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Ka, J.-W.1
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Lee, C.-H.3
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