A new approach to aromatic substitution - para-specific alkylation of acetophenone by alkyl radicals in strongly acidic media

Laily Bin Din, Otto Meth-Cohn, Nigel D A Walshe

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Acetophenone in 25% oleum is substituted by various alkyl radicals specifically in the para-position. The radicals used include cyclohexyl, 3-chloro-1-methylpropyl, 3-bromo-1-methylpropyl, 4-chloro-1-methylbutyl, 4-bromo-1-methylbutyl, 5-bromo-1-methylpentyl, 5-acetoxy-1-methylpentyl, 3-carboxy-1-methylpropyl, 4-carboxy-1-methylbutyl and 5-carboxy-1-methylpentyl. They were all generated by hydrogen atom abstraction at the radical position by dimethylaminium radicals, generated in turn from protonated dimethylchloramine and ferrous sulphate. Yields were generally poor to moderate but utilised simple conditions and cheap reagents.

Original languageEnglish
Pages (from-to)781-786
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
Publication statusPublished - 1991
Externally publishedYes

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ferrous sulfate
Alkylation
Hydrogen
Substitution reactions
Atoms
acetophenone

ASJC Scopus subject areas

  • Chemistry(all)

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A new approach to aromatic substitution - para-specific alkylation of acetophenone by alkyl radicals in strongly acidic media. / Din, Laily Bin; Meth-Cohn, Otto; Walshe, Nigel D A.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 4, 1991, p. 781-786.

Research output: Contribution to journalArticle

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