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(c) We also examined the use of a tert-butyl amide in this context, and found it to be unsuitable.
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For a discussion of the mechanism of the lithium hydroperoxide cleavage of active esters, cf. ref. 13a.
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0342395830
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2) conditions. (b) Vilarassa and co-workers have postulated that nitrosation favors the carbamate at short reaction times with nitrogen dioxide, and that these N-nitroso carbamates may be degraded with acid. Thus, nitrosation with nitrogen dioxide in acetic acid for prolonged time favors nitrosation of the amide residue. cf. Ref. 18 for a complete discussion of these results.
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0342830632
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note
-
2O and DMAP afforded the opposite selectivity, giving N-Boc N-methylbenzamide and N-Boc benzamide in a 1:9 ratio. To the best of our knowledge, this sense of selectivity has not been documented previously.
-
-
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35
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0027417977
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(b) It has been shown that primary amides are nitrosated more readily than hindered (isopropyl) secondary amides: Okuyama, S.; Kamachi, H.; Oki, T. Chem. Pharm. Bull. 1993, 41, 223-225; and Webster, F. X.; Millar, J. G.; Silverstein, R. M. Tetrahedron Lett. 1986, 27, 4941-4944.
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(b) It has been shown that primary amides are nitrosated more readily than hindered (isopropyl) secondary amides: Okuyama, S.; Kamachi, H.; Oki, T. Chem. Pharm. Bull. 1993, 41, 223-225; and Webster, F. X.; Millar, J. G.; Silverstein, R. M. Tetrahedron Lett. 1986, 27, 4941-4944.
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