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0345051431
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in press
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2-porphyrin.
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0345051428
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note
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During this study we found that use of analytically pure dipyrromethanes, prepared as described in ref 12, was imperative to achieve both the highest yields and the minimum scrambling.
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34
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Li, F.; Yang, K.; Tyhonas, J. S.; MacCrum, K. A.; Lindsey, J. S. Tetrahedron 1997, 53, 12339-12360.
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35
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0344189167
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-
note
-
The stoichiometry of the dipyrromethane-aldehyde condensation requires 1.5 mol of DDQ per 1 mol of dipyrromethane (giving 3 mol of DDQ per 1 mol of porphyrinogen). We have found that the oxidation can often be performed with less than the stoichiometric amount (1 mol of DDQ per 1 mol of dipyrromethane) without a decrease in the porphyrin yield or change in chlorin content. With 0.5 mol of DDQ per 1 mol of dipyrromethane, the yield did decline and the amount of chlorin increased.
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37
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For examples see: (a) Wallace, D. M.; Leung, S. H.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1993, 58, 7245-7257.
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0344189166
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note
-
This example illustrates that mass spectrometry is a more reliable method for determination of the presence or absence of scrambling.
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45
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0000925615
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