Electrolytically induced allene-alkyne isomerizations

JZ Stemple, DG Peters

Index: Stemple, Joseph Z.; Peters, Dennis G. Journal of Organic Chemistry, 1989 , vol. 54, # 22 p. 5318 - 5323

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Citation Number: 10

Abstract

Preparative-scale electrolyses at mercury cathodes in dimethylformamide containing tetra-n- butylammonium perchlorate have revealed that l-phenyl-1, 2-hexadiene exhibits no evidence of isomerization to form 1-phenyl-1-hexyne via an electrolytically induced, base- catalyzed rearrangement; similarly, l-phenyl-l, 2-butadiene exhibits only a slight tendency (1- 2%) to form 1-phenyl-1-butyne. In contrast, voltammetric and electrolytic experiments ...