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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400259