The mechanism of lithiation and nitrile insertion reactions of β-methylazines: Evidence from the structure of 3-C5H4NCH=C(Ph)N(H)C(Ph)=NLi · PMDETA

Sarah C. Ball; Robert P. Davies; Paul R. Raithby; Gregory P. Shields; Ronald Snaith

doi:10.1016/S0022-328X(97)00553-6

The mechanism of lithiation and nitrile insertion reactions of β-methylazines: Evidence from the structure of 3-C₅H₄NCH=C(Ph)N(H)C(Ph)=NLi · PMDETA

Sarah C. Ball, Robert P. Davies, Paul R. Raithby, Gregory P. Shields, Ronald Snaith

University of Cambridge

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

21 Citations (SciVal)

Abstract

A 1:1:1 reaction of 3-methylpyridine, 1, with LDA and PhCN in the presence of PMDETA gives the title complex 6, shown by X-ray crystallography to be the first monomeric iminolithium. The isolation of 6, and of a cyclised product 8 when a 3:10:3 reaction of 1:LDA:PhCN is carried out, suggest a mechanism for previously published cyclisation reactions of β-methylazines.

Original language	English
Pages (from-to)	457-461
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	550
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(97)00553-6
Publication status	Published - 15 Jan 1998

Funding

We thank the EPSRC (S.C.B., R.P.D., G.P.S.), the CCDC (G.P.S.), the Associated Octel Co. Ltd. (S.C.B.) and the Royal Society (low-temperature X-ray diffraction apparatus, P.R.R.) for financial support.

Keywords

Lithium
Nitriles
Reaction mechanisms
X-ray structure

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Access to Document

10.1016/S0022-328X(97)00553-6

Cite this

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title = "The mechanism of lithiation and nitrile insertion reactions of β-methylazines: Evidence from the structure of 3-C5H4NCH=C(Ph)N(H)C(Ph)=NLi · PMDETA",

abstract = "A 1:1:1 reaction of 3-methylpyridine, 1, with LDA and PhCN in the presence of PMDETA gives the title complex 6, shown by X-ray crystallography to be the first monomeric iminolithium. The isolation of 6, and of a cyclised product 8 when a 3:10:3 reaction of 1:LDA:PhCN is carried out, suggest a mechanism for previously published cyclisation reactions of β-methylazines.",

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T2 - Evidence from the structure of 3-C5H4NCH=C(Ph)N(H)C(Ph)=NLi · PMDETA

AU - Ball, Sarah C.

AU - Davies, Robert P.

AU - Raithby, Paul R.

AU - Shields, Gregory P.

AU - Snaith, Ronald

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N2 - A 1:1:1 reaction of 3-methylpyridine, 1, with LDA and PhCN in the presence of PMDETA gives the title complex 6, shown by X-ray crystallography to be the first monomeric iminolithium. The isolation of 6, and of a cyclised product 8 when a 3:10:3 reaction of 1:LDA:PhCN is carried out, suggest a mechanism for previously published cyclisation reactions of β-methylazines.

AB - A 1:1:1 reaction of 3-methylpyridine, 1, with LDA and PhCN in the presence of PMDETA gives the title complex 6, shown by X-ray crystallography to be the first monomeric iminolithium. The isolation of 6, and of a cyclised product 8 when a 3:10:3 reaction of 1:LDA:PhCN is carried out, suggest a mechanism for previously published cyclisation reactions of β-methylazines.

KW - Lithium

KW - Nitriles

KW - Reaction mechanisms

KW - X-ray structure

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