Conjugate addition of grignard reagents to para-substituted nitrobenzenes

Nitrobenzenes bearing masked aldehyde, ketone and ketoester functions at the 4-position undergo conjugate addition with Grignard reagents in THF at − 15°C. Sequential treatment of the 4-substituted nitrobenzenes with primary or secondary alkyl magnesium halides followed by 2,3-dichloro-5,6-dicyano-1...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 447; no. 1; pp. 1 - 3
Main Authors Bentley, Stephen J., Milner, David J.
Format Journal Article
LanguageEnglish
Published Lausanne Elsevier B.V 01.03.1993
Elsevier Science
Subjects
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
1,2-Benzoquinone-2,3-dicarbonitrile(dichloro)
Nitro compound
Benzenic compound
Grignard reaction
THF
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Summary:Nitrobenzenes bearing masked aldehyde, ketone and ketoester functions at the 4-position undergo conjugate addition with Grignard reagents in THF at − 15°C. Sequential treatment of the 4-substituted nitrobenzenes with primary or secondary alkyl magnesium halides followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone affords the corresponding 2-alkylated derivatives in 50–80% yields.
ISSN:0022-328X
1872-8561
DOI:10.1016/0022-328X(93)80265-D