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Intermediates of this type have also been isolated in the 1,2,3-triazole series: Smith, P. A. S.; Krbechek, L. O.; Resemann, W. J. Am. Chem. Soc. 1984, 86, 2025-2033.
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The acid chlorides 4a,b are commercially available, whereas acid chloride 4c was prepared by the standard procedure using thionyl chloride in toluene. See for example: Miller, W. H.; Dessert, A. M.; Anderson, G. W. J. Am. Chem. Soc. 1948, 70, 500-502.
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The preparation of compound 8a has been claimed in the literature, but no spectroscopic or physical data were reported: Tietze, L. F.; Steinmetz, A.; Balkenhohl, F. Bioorg. Med. Chem. Lett. 1997, 7, 1303-1306.
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27
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0345051487
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note
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The authors have deposited atomic coordinates and thermal parameters for 2b and 3b with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
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Interestingly, this procedure appears to produce the keto form exclusively, as opposed to a similar procedure that produces a mixture of the keto an enol forms: Capozzi, G.; Roelens, S.; Talami, S. J. Org. Chem. 1993, 58, 7932-7936.
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Capozzi, G.1
Roelens, S.2
Talami, S.3
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