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M. C. Feiters, in Comprehensive Supramolecular Chemistry, eds., J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogtle, D. N. Reinhoudt, and, J.-M. Lehn, Pergamon, Elmsford, 1996, vol. 10, pp. 267-360
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J. Nakazawa J. Hagiwara M. Mizuki Y. Shimazaki F. Tani Y. Naruta Angew. Chem., Int. Ed. 2005 44 3744 3746
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Tani, F.5
Naruta, Y.6
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E. F. Maverick and D. J. Cram, in Comprehensive Supramolecular Chemistry, eds., J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogtle, D.N. Reinhoudt, and, J.-M. Lehn, Pergamon, Elmsford, 1996, vol. 2, pp. 367-418
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Maverick, E.F.1
Cram In, D.J.2
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The TPP derivative used consists as a mixture of four isomers, varying only in the orientation of the o-hydroxy groups. Isomerisation occurs at room temperature, and reflux of the reaction solution, as observed by Naruta and co-workers. This results in the correct orientation (over a period of days) of all the hydroxy groups to afford coupling of the porphyrin with the resorcin[4]arene. Altering reflux temperatures and lengths were among the changes made to protocol
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The TPP derivative used consists as a mixture of four isomers, varying only in the orientation of the o-hydroxy groups. Isomerisation occurs at room temperature, and reflux of the reaction solution, as observed by Naruta and co-workers. This results in the correct orientation (over a period of days) of all the hydroxy groups to afford coupling of the porphyrin with the resorcin[4]arene. Altering reflux temperatures and lengths were among the changes made to protocol
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70349282190
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Preparation of supramolecularly capped porphyrins from aldehyde precursors such as 3 and 4 has been shown to proceed via two synthetic pathways. The most common of these two methods makes use of the Adler conditions; the addition of pyrrole to the aldehyde followed by condensation in an acidic medium (propionic acid) at reflux temperatures (140 °C) under aerobic conditions. In contrast, the gentler Lindsey conditions make use of a Lewis acid catalyst and dry, inert reaction conditions. This latter protocol has found only limited application. However, observations by Reinhoudt et al. indicated that porphyrin formation using this cyclisation technique was significantly dependant on the synthetic conditions employed. Ligands bearing shorter bridges formed exclusively on application of the Adler conditions, whilst ligands bearing longer bridges exclusively on application of the Lindsey conditions
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Preparation of supramolecularly capped porphyrins from aldehyde precursors such as 3 and 4 has been shown to proceed via two synthetic pathways. The most common of these two methods makes use of the Adler conditions; the addition of pyrrole to the aldehyde followed by condensation in an acidic medium (propionic acid) at reflux temperatures (140 °C) under aerobic conditions. In contrast, the gentler Lindsey conditions make use of a Lewis acid catalyst and dry, inert reaction conditions. This latter protocol has found only limited application. However, observations by Reinhoudt et al. indicated that porphyrin formation using this cyclisation technique was significantly dependant on the synthetic conditions employed. Ligands bearing shorter bridges formed exclusively on application of the Adler conditions, whilst ligands bearing longer bridges exclusively on application of the Lindsey conditions
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44
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33845184181
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L. M. Tunstad J. A. Tucker E. Dalcanale J. Weiser J. A. Bryant J. C. Sherman R. C. Helgeson C. B. Knobler D. J. Cram J. Org. Chem. 1989 54 1305 1312
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Tunstad, L.M.1
Tucker, J.A.2
Dalcanale, E.3
Weiser, J.4
Bryant, J.A.5
Sherman, J.C.6
Helgeson, R.C.7
Knobler, C.B.8
Cram, D.J.9
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47
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0023212189
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H. Nate K. Matsuki A. Tsunashima H. Ohtsuka Y. Sekine K. Oda Y. Honma A. Ishida H. Nakai H. Wada M. Takeda H. Yabana T. N. Y. Hino Chem. Pharm. Bull. 1987 35 2394 2411
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Nate, H.1
Matsuki, K.2
Tsunashima, A.3
Ohtsuka, H.4
Sekine, Y.5
Oda, K.6
Honma, Y.7
Ishida, A.8
Nakai, H.9
Wada, H.10
Takeda, M.11
Yabana, H.12
Hino, T.N.Y.13
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59
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70349274386
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The microwave synthesis unit used did not allow for variable power output. Additionally, the borosilicate reaction vessels used were of a fixed volume, which limited studies of the effect of varied reagent concentration on yield
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The microwave synthesis unit used did not allow for variable power output. Additionally, the borosilicate reaction vessels used were of a fixed volume, which limited studies of the effect of varied reagent concentration on yield
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Optimum yields were obtained for a reagent concentration of 0.01 M (with respect to aldehyde precursor). Increasing concentrations to 0.02 M (at every temperature) had no observable effect on yield
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Optimum yields were obtained for a reagent concentration of 0.01 M (with respect to aldehyde precursor). Increasing concentrations to 0.02 M (at every temperature) had no observable effect on yield
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