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ChemInform Abstract: Unusual Example of Nucleophilic Substitution in Nitrophthalimide Series.

✍ Scribed by E. V. KUDRIK; M. A. ZHARNIKOVA; E. A. DERYABKINA; G. P. SHAPOSHNIKOV

Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Unusual Example of Nucleophilic Substitution in Nitrophthalimide

Series.

-The reaction of 3-(I) and 4-nitrophthalimides (III) with hydroxylamine is studied. While 4-nitrophthalimide (III) undergoes amination in both the neighboring positions relative to the nitro group affording a mixture of the regioisomers (IV) and (V), the 3-nitro analogue (I) affords unexpectedly the 3,6-dihydroxyphthalimide (II). A possible reaction mechanism that explains this unexpected substitution is given. -(KUDRIK, E. V.; ZHARNIKOVA,

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