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Issue 26, 2013
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The heterocyclic ring of 4-substituted-1,8-naphthalimides is NOT inert to nucleophilic attack, contrary to earlier reports

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Abstract

The heterocyclic ring of N-aryl-4-chloro-1,8-naphthalimides, reported to be resistant to nucleophilic attack, reacts with primary amine nucleophiles at room temperature to give 4-chloro-N-alkyl-1,8-naphthalimides. The reaction is first order in the naphthalimide. The Hammett plot is linear (R2 0.996) with a large positive slope (+3.0), consistent with substantial negative charge development at nitrogen in the activated complex.

Graphical abstract: The heterocyclic ring of 4-substituted-1,8-naphthalimides is NOT inert to nucleophilic attack, contrary to earlier reports

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Publication details

The article was received on 30 Mar 2013, accepted on 20 May 2013 and first published on 21 May 2013


Article type: Paper
DOI: 10.1039/C3OB40639C
Citation: Org. Biomol. Chem., 2013,11, 4390-4396
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    The heterocyclic ring of 4-substituted-1,8-naphthalimides is NOT inert to nucleophilic attack, contrary to earlier reports

    R. K. McKenney, L. L. Groess, K. M. Kopidlansky, K. L. Dunkle and D. E. Lewis, Org. Biomol. Chem., 2013, 11, 4390
    DOI: 10.1039/C3OB40639C

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