Delocalized carbanions. V. Tetraanion from the lithium reduction of cis, cis-1, 2, 3, 4-tetraphenylbutadiene

VR Sandel, B Belinky, T Stefaniak…

Index: Sandel,V.R. et al. Journal of Organic Chemistry, 1975 , vol. 40, # 14 p. 2116 - 2120

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Citation Number: 6

Abstract

The reduction of cis, cis-1, 2, 3, 4-tetraphenylbutadiene with lithium in tetrahydrofuran yields 1, 2, 3, 4-tetralithio-1, 2, 3, 4-tetraphenylbutane, which upon hydrolysis with DzO gives dl- and meso-1, 2, 3, 4-tetradeuterio-1, 2, 3, 4-tetra-phenylbutane in yields up to 86%. The progress of the reduction was followed through the radical anion and dianion stages to the tetraanion by EPR and uv-visible spectroscopy. No trianion radical intermediate was ...