C-alkylation of β diketones with benzylpyridinium salts. Evidence for chain radical mechanisms

Jorge Marquet, Marcial Moreno-Mañas, Pedro Pacheco, Maria Prat, Alan R. Katritzky, Bogumil Brycki

Research output: Contribution to journalArticleResearchpeer-review

24 Citations (Scopus)

Abstract

1-(p-Substituted benzyl)-2,4,6-triphenylpyridinium cations react with β -diketone anions by mechanisms which depend on the para-substituent. The p-methoxybenzyl derivative undergoes SN1 displacement yielding O- and C-benzylated products. The pnitrobenzyl compound reacts by a chain radicaloid mechanism and gives high yields of C-pnitrobenzylated diketones. The parent benzyl compound forms some C- and some O-benzylated products, together with bibenzyl, probably by a radical chain reaction which was suppressed by radical traps. © 1990.
Original languageEnglish
Pages (from-to)5333-5346
JournalTetrahedron
Volume46
Issue number15
DOIs
Publication statusPublished - 1 Jan 1990

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