Tetrahedron Letters

Nitration of tert-butyloxycarbonylated aniline and 1, 3, 5-triaminobenzene by acetyl nitrate

MC Davis, TJ Groshens

Index: Davis, Matthew C.; Groshens, Thomas J. Tetrahedron Letters, 2012 , vol. 53, # 32 p. 4154 - 4155

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Citation Number: 1

Abstract

The aromatic nitration of aniline is difficult owing to its inherent sensitivity to oxidation as well as deactivation toward electrophilic substitution through formation of its ammonium salt by the acidic conditions typically employed. 1 For best results, a protecting group for the amine should be employed that is both convenient to install and later remove. Carboxyl- 2 and sulfonylamides 3 as well as alkyl carbamate (methyl and ethyl) 4 have been used for this purpose but ...

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