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Revisiting the Schlenk Dimerisation Reaction of 1,1-Diphenylethene

Lookup NU author(s): Dr Mo Liu, Dr Ahmed Alwaaly, Dr Paul Waddell, Dr Keith IzodORCiD

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Abstract

The reaction between 1,1-diphenylethene and two equivalents of lithium in THF gave the complex [(Ph₂CCH₂CH₂CPh₂)Li₂(THF)₄] (3), which crystallised from Et₂O/THF as the dialkyllithate salt [Li(THF)₄][(Ph₂CCH₂CH₂CPh₂)Li(THF)] (3a). A similar reaction between 1,1-diphenylethene and sodium metal in THF gave [(Ph₂CCH₂CH₂CPh₂)Na₂(THF)_1.5] (4), which crystallised from THF as the polymer [(Ph₂CCH₂CH₂CPh₂)Na₂(THF)₃]_¥ (4a). In contrast, reactions between 1,1-diphenylethene and potassium under the same conditions gave intractable mixtures of products. However, treatment of 3 with two equivalents of KOtBu in THF yielded the complex [(Ph₂CCH₂CH₂CPh₂)K₂(THF)_0.5] (5) as a deep red powder; treatment of 5 with two equivalents of 12-crown-4, followed by crystallisation from methylcyclohexane/THF, gave the adduct [(Ph₂CCH₂CH₂CPh₂)K₂(THF)₂(12-crown-4)₂] (5a). A similar reaction between 3 and 12-crown-4 gave the separated ion pair [Li(THF)(12-crown-4)][Li(THF)_0.5(OEt₂)_0.5(12-crown-4)][(Ph₂CCH₂CH₂CPh₂)] (3b), which contains the free 1,1,4,4-tetraphenyl-1,4-butanediide dicarbanion. X-ray crystallography revealed that the C₃C centres of the ligands adopt a near planar geometry, irrespective of whether a metal cation is in close contact.

Publication metadata

Author(s): Liu M, Alwaaly A, Waddell PG, Izod K

Publication type: Article

Publication status: Published

Journal: Journal of Organometallic Chemistry

Year: 2023

Volume: 1001

Print publication date: 15/11/2023

Online publication date: 19/08/2023

Acceptance date: 17/08/2023

Date deposited: 07/09/2023

ISSN (print): 0022-328X

ISSN (electronic): 1872-8561

Publisher: Elsevier BV

URL: https://doi.org/10.1016/j.jorganchem.2023.122865

DOI: 10.1016/j.jorganchem.2023.122865

Data Access Statement: Data will be made available on request.

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