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Regiospecific substitution of the 4-nitro group in 3-amino-4,6-dinitrobenzo[b]thiophene-2-carboxylates: unexpected activating effect of the amino group

✍ Scribed by Svyatoslav A Shevelev; Igor L Dalinger; Tatyana I Cherkasova

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 70 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01833-0

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✦ Synopsis

The cyclocondensation of 2,4,6-trinitrobenzonitrile with the esters of thioglycolic acid results in the formation of 3-amino-4,6-dinitrobenzo[b]thiophene-2-carboxylates 3. The interaction of 3 with anionic nucleophiles RO

-in NMP or DMF leads to the substitution of only the 4-NO 2 group. The replacement of the electron-donating NH 2 group in 3 with hydrogen unexpectedly and significantly hampers nucleophilic substitution of the nitro group. It is assumed that increased reactivity of the 4-NO 2 in 3 is connected with the twist of this group with respect to the plane of the aromatic ring under the influence of the NH 2 group as indicated by semi-empirical quantum chemical calculations.

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