Metalation reactions-XVII. The dimetalation of branched olefins. The question of the aromaticity of the trimethylenemethane dianion and related derivatives

J. Klein; A. Medlik-Balan; A. Y. Meyer; M. Chorev

doi:10.1016/0040-4020(76)85183-6

Metalation reactions-XVII. The dimetalation of branched olefins. The question of the aromaticity of the trimethylenemethane dianion and related derivatives

J. Klein^*
, A. Medlik-Balan
, A. Y. Meyer
, M. Chorev

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

Metalation of methallylbenzenes with BuLi gave dilithio derivatives which were dialkylated with methyl bromide. Derivatives of cross conjugated dianions are obtained preferentially to linear ones. The parent trimethylenemethane dianion² was obtained by metalation of isobutene. Energies and atomic net charges of these and related molecules were calcualted. The question of the aromaticity of these systems is discussed.

Original language	English
Pages (from-to)	1839-1847
Number of pages	9
Journal	Tetrahedron
Volume	32
Issue number	14
DOIs	https://doi.org/10.1016/0040-4020(76)85183-6
State	Published - 1976

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abstract = "Metalation of methallylbenzenes with BuLi gave dilithio derivatives which were dialkylated with methyl bromide. Derivatives of cross conjugated dianions are obtained preferentially to linear ones. The parent trimethylenemethane dianion2 was obtained by metalation of isobutene. Energies and atomic net charges of these and related molecules were calcualted. The question of the aromaticity of these systems is discussed.",

author = "J. Klein and A. Medlik-Balan and Meyer, \{A. Y.\} and M. Chorev",

year = "1976",

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AU - Meyer, A. Y.

AU - Chorev, M.

PY - 1976

Y1 - 1976

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AB - Metalation of methallylbenzenes with BuLi gave dilithio derivatives which were dialkylated with methyl bromide. Derivatives of cross conjugated dianions are obtained preferentially to linear ones. The parent trimethylenemethane dianion2 was obtained by metalation of isobutene. Energies and atomic net charges of these and related molecules were calcualted. The question of the aromaticity of these systems is discussed.

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Metalation reactions-XVII. The dimetalation of branched olefins. The question of the aromaticity of the trimethylenemethane dianion and related derivatives

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