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33644648568
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The unusual profile observed for the conversion of 2 to 3 cannot be fully explained at this time.
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38
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33644647892
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The product of transfer hydrogenation, 2,2-dimethylbutane, was also detected at levels commensurate with 4 formation.
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The role of the acid additive in accelerating catalysis has not yet been ascertained.
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44
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33644637323
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4f
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45
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33644641055
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4f compared to coupling reactions of less substituted olefins.
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46
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Isomeric mixtures were separated by chromatography.
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49
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4243764636
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37b,c have been used for the synthesis of 1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolines: (a) Karimov, A.; Telezhenetskaya, M. V.; Yunusov, S. Y. Khim. Prir. Soedin. 1982, 18, 498.
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33644655218
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We also considered altering our synthetic route by exchanging the dimethylamino group for an N-protected amino group. These efforts led to lengthy reaction sequences.
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69
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33644651560
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This two-step sequence was preferred to direct reduction of o-chlorocinnamic acid because common procedures for carboxylic acid reduction gave competitive conjugate reduction.
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70
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33644652683
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note
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3 method is more amenable to use on large scale.
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6344253335
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Forman, G. S.; McConnell, A. E.; Hanton, M. J.; Slawin, A. M. Z.; Tooze, R. P.; van Rensburg, W. J.; Meyer, W. H.; Dwyer, C.; Kirk, M. M.; Serfontein, D. W. Organometallics 2004, 23, 4824.
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72
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33644653251
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Cy-[3.3.1]-Phoban was prepared in moderate yield by alkylation of H-[3.3.1]-Phoban with BuLi/CyBr: (a) Meyer, W. H. Personal communication.
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Meyer, W.H.1
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33644640925
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2 with 1,5-cyclooctadiene (see ref 42).
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33644651249
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A synthesis of the -Br analogue of 23 was undertaken starting from 2-bromocinnamic acid. The method used to prepare 23 proved ineffective in this effort; the Rh-catalyzed cyclization step produced an uncharacterized mixture of decomposition products.
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77
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0033597748
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47b have been reported: (a) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
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