The reaction of 3,4-dinitrothiophene with Grignard reagents: Formation of 2-(3-amino-4-nitrothiophen-2-yl)phenols

被引：7

作者：

Bianchi, L ^{[1
]}

Dell'Erba, C ^{[1
]}

Maccagno, M ^{[1
]}

Mugnoli, A ^{[1
]}

Novi, M ^{[1
]}

Petrillo, G ^{[1
]}

Severi, E ^{[1
]}

Tavani, C ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 16期

关键词：

nitrothiophenes; 3,4-dinitrothiophene; Grignard reagents; Claisen-like rearrangements;

D O I：

10.1002/ejoc.200400259

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of 3,4-dinitrothiophene with an aryl Grignard reagent results in the reduction of one nitro group accompanied by the ipso-substitution of a hydrogen atom by an orthophenolic group on the ring carbon adjacent to the reduced nitro group. A Claisen-type intramolecular rearrangement is proposed as the pivotal step of a rather complex mechanism, followed by proton-transfer aromatizing steps. This work shows yet another facet of the variegated reactivity of 3,4-dinitrothiophene towards nucleophiles. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

引用

页码：3566 / 3570

页数：5

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