The Reaction of 3,4-Dinitrothiophene with Grignard Reagents: Formation of 2-(3-Amino-4-nitrothiophen-2-yl)phenols

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 ortho‐phenolic group on the ring carbon adjacent to the reduced nitro group. A Claisen‐type intramolecular rearrangement is pr...

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Published in:European journal of organic chemistry 2004-08, Vol.2004 (16), p.3566-3570
Main Authors: Bianchi, Lara, Dell'Erba, Carlo, Maccagno, Massimo, Mugnoli, Angelo, Novi, Marino, Petrillo, Giovanni, Severi, Elda, Tavani, Cinzia
Format: Article
Language:English
Subjects:
3,4‐Dinitrothiophene
4-Dinitrothiophene
Claisen-like rearrangements
Grignard reagents
Nitrothiophenes
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container_issue 16
container_start_page 3566
container_title European journal of organic chemistry
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creator Bianchi, Lara
Dell'Erba, Carlo
Maccagno, Massimo
Mugnoli, Angelo
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Petrillo, Giovanni
Severi, Elda
Tavani, Cinzia
description 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 ortho‐phenolic 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
doi_str_mv 10.1002/ejoc.200400259
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subjects 3,4‐Dinitrothiophene
4-Dinitrothiophene
Claisen-like rearrangements
Grignard reagents
Nitrothiophenes
title The Reaction of 3,4-Dinitrothiophene with Grignard Reagents: Formation of 2-(3-Amino-4-nitrothiophen-2-yl)phenols
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