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We chose oxalyl chloride for ease of handling but also screened alternative agents to effect a similar reaction. Of these, triphosgene and phosphorus pentachloride provided positive data points, while thionyl chloride and phosphoryl chloride did not. For a related reference, see: Chauvette, R. R, Pennington, P. A, Ryan, C. W, Cooper, R. D. G, José, F. L, Wright, I. G, Van Heyningen, E. M, Huffman, G. W. J. Org. Chem. 1971, 36, 1259
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We chose oxalyl chloride for ease of handling but also screened alternative agents to effect a similar reaction. Of these, triphosgene and phosphorus pentachloride provided positive data points, while thionyl chloride and phosphoryl chloride did not. For a related reference, see: Chauvette, R. R.; Pennington, P. A.; Ryan, C. W.; Cooper, R. D. G.; José, F. L.; Wright, I. G.; Van Heyningen, E. M.; Huffman, G. W. J. Org. Chem. 1971, 36, 1259.
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2 has been used to form other adducts with amides. For related references, see: (a) Sheehan, J. C.; Corey, E. J. J. Am. Chem. Soc. 1952, 74, 360.
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2 has been used to form other adducts with amides. For related references, see: (a) Sheehan, J. C.; Corey, E. J. J. Am. Chem. Soc. 1952, 74, 360.
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62149131879
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This material was not further characterized
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This material was not further characterized.
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42
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62149133151
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Acetamide 2 was run successfully at 40 kg scale.
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Acetamide 2 was run successfully at 40 kg scale.
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43
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