The Journal of Organic Chemistry

Convenient preparation of 1, 3-bis (2, 3, 4, 5-tetramethylcyclopentadienyl) propane. 2, 3, 4, 5-Tetramethyl-2-cyclopentenone enolate as a synthetic equivalent for the …

EA Mintz, JC Pando, I Zervos

Index: Mintz, Eric A.; Pando, Jerome C.; Zervos, Irene Journal of Organic Chemistry, 1987 , vol. 52, # 13 p. 2948 - 2950

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Citation Number: 9

Abstract

pentadiene (5). Treatment of 1 with LiN (iC, H,), followed by alkylation with benzyl chloride produces the benzyl ketone 3 in high yield (Scheme I). Reduction of 3 with LiA1H4 produces the corresponding alcohol 4 which upon treatment with p-toluenesulfonic acid in refluxing benzene undergoes dehydration and Wagner-Meerwein rearrangement to give benzyl-2, 3, 4, 5-tetramethylcyclo-pentadiene (5) in 64% overall yield based on enone 1. In an ...