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2 in DMF as the solvent, the ring-annulated product was obtained in up to 95% yield. During the reviewing process, a similar cyclization reaction was reported, however, with lower yields: Shen, D.-M.; Liu, C.; Chen, Q.-Y. J. Org. Chem. 2006, 71, 6508.
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1842731111
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A similar behavior was also observed in meso-β-linked bisporphyrins and corroborated by a crystal structure: Senge, M. O.; Rößler, B.; von Gersdorff, J.; Schäfer, A.; Kurreck, H. Tetrahedron Lett. 2004, 45, 3363.
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33750340828
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note
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1H NMR spectrum of TPP is available in the Supporting Information.
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25
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0842341771
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33750304993
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note
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Further chromatographic details: using a Chiralcel OD-H column (Daicel), 7°C, a flow rate of 0.3 mL/min, and n-hexane/2-propanol = 60: 40 as the eluent, or even more efficiently in the case of 4b, using a Chirex 3010 column (Phenomenex), 25°C, a flow rate of 1 mL/min, and n-hexane/ dichloromethane = 60:40 as the eluent.
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29
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note
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This chromatographic order is true for both chiral adsorbants used, Chiralcel OD-H (Daicel) and Chirex 3010 (Phenomenex).
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0000750794
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Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden
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note
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Because Zn is not parametrized in the program packages that were used for the semiempirical calculation of excited states, the metal-free analogue of 4a was investigated instead. This approximation seemed justified because the presence or absence of Zn should not influence the shape of the CD curve substantially.
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35
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To verify this assumption, three additional PM3 minimum geometries were also optimized with B3LYP/3-21G providing CD spectra identical to the one of the global minimum.
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38
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33750316648
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note
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2-symmetry, the same applies for the phenyl group at C-5′ (which, in turn, is bent away from the porphyrin substituent at C-3′).
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0039209924
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