Reactions of organolithium complexes with elemental selenium: Insertion producing [PhCCSeLi · TMEDA · THF] 1 and cyclisation producing [{PhC}4Se] 2 (TMEDA=[Me2NCH2]2)1

Michael A. Beswick; Christopher N. Harmer; Paul R. Raithby; Alexander Steiner; Mustafa Tombul; Dominic S. Wright

doi:10.1016/S0022-328X(98)00830-4

Reactions of organolithium complexes with elemental selenium: Insertion producing [PhCCSeLi · TMEDA · THF] 1 and cyclisation producing [{PhC}₄Se] 2 (TMEDA=[Me₂NCH₂]₂)¹

Michael A. Beswick, Christopher N. Harmer, Paul R. Raithby, Alexander Steiner, Mustafa Tombul, Dominic S. Wright

University of Cambridge

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

21 Citations (SciVal)

Abstract

The reaction of [PhCCLi]_n with Se metal (1:1 equivalents) in THF/TMEDA gives the insertion product [PhCCSeLi · TMEDA · THF] 1, which is monomeric in the solid state. The reaction of PhCCPh with Li metal, generating dilithium tetraphenylbutadiene in situ, followed by the addition of elemental Se gives the selenophene [{PhC}₄Se] 2, as a result of insertion of Se followed by the elimination of Li₂Se. The latter provides a clean and direct route to compounds of this type.

Original language	English
Pages (from-to)	267-271
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	573
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(98)00830-4
Publication status	Published - 31 Jan 1999

Funding

We gratefully acknowledge the EPSRC (M.A.B., C.N.H., P.R.R., D.S.W.), the European Community (fellowship for A.S.), the Leverhulme Trust (M.A.B.), The Royal Society (P.R.R., D.S.W.) and the Turkish Government (M.T.) for financial support.

Keywords

Organolithium
Organoselenides
Selenophene

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Access to Document

10.1016/S0022-328X(98)00830-4

Cite this

Reactions of organolithium complexes with elemental selenium: Insertion producing [PhCCSeLi · TMEDA · THF] 1 and cyclisation producing [{PhC}₄Se] 2 (TMEDA=[Me₂NCH₂]₂)¹. / Beswick, Michael A.; Harmer, Christopher N.; Raithby, Paul R. et al.
In: Journal of Organometallic Chemistry, Vol. 573, No. 1-2, 31.01.1999, p. 267-271.

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

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abstract = "The reaction of [PhCCLi]n with Se metal (1:1 equivalents) in THF/TMEDA gives the insertion product [PhCCSeLi · TMEDA · THF] 1, which is monomeric in the solid state. The reaction of PhCCPh with Li metal, generating dilithium tetraphenylbutadiene in situ, followed by the addition of elemental Se gives the selenophene [{PhC}4Se] 2, as a result of insertion of Se followed by the elimination of Li2Se. The latter provides a clean and direct route to compounds of this type.",

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AU - Beswick, Michael A.

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