Formation of peralkylcyclohexadienyllithium compounds

M Hallden-Abberton, C Engelman…

Index: Hallden-Abberton, Michael; Engelman, Carl; Fraenkel, Gideon Journal of Organic Chemistry, 1981 , vol. 46, # 3 p. 538 - 546

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Citation Number: 7

Abstract

1, 1, 2, 3, 5, 6-Hexamethyl-4-methylene-2, 5-cyclohe~ diene (1) reacts with alkyllithium compounds, RLi (R= n-Bu, sec-Bu, and t-Bu), at 20 “C in hydrocarbon solution or in the presence of ethers or tertiary amines, which act as ligands, to give stable, soluble 1, 1, 2, 3, 5, 6-hexamethyl-4-alkylcyclohexadienyllithium compounds, 3a-c. On heating, the latter aromatize to pentamethylalkylbenzenes, 4a-q with extrusion of methyllithium, while on ...