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In the case of 2, a small amount (ca. 10, of the 9,10-diphenyl substituted species (2″) was consistently observed, the structure of which was confirmed by NMR, mass spectrometry, and X-ray crystallography see Figure S3, Supporting Information, At present, we do not know how this compound is formed; ongoing mechanistic experiments suggest that solvent does not play a significant role, that the process is not influenced by adventitious HCl, and that residual palladium in the pyridine compound is likely not involved
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In the case of 2, a small amount (ca. 10%) of the 9,10-diphenyl substituted species (2″) was consistently observed, the structure of which was confirmed by NMR, mass spectrometry, and X-ray crystallography (see Figure S3, Supporting Information). At present, we do not know how this compound is formed; ongoing mechanistic experiments suggest that solvent does not play a significant role, that the process is not influenced by adventitious HCl, and that residual palladium in the pyridine compound is likely not involved.
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NICS(1) values of -10.2 (inner) and -6.5 ppm (outer) have been previously reported for phenanthrene: Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.
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NICS(1) values of -10.2 (inner) and -6.5 ppm (outer) have been previously reported for phenanthrene: Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.
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