Tetrahedron

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

…, P Pacheco, M Prat, AR Katritzky, B Brycki

Index: Marquet, Jorge; Moreno-Manas, Marcial; Pacheco, Pedro; Prat, Maria; Katritzky, Alan R.; Brycki, Bogumil Tetrahedron, 1990 , vol. 46, # 15 p. 5333 - 5346

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Citation Number: 20

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- ...

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