The mechanisms of dilithiation reactions in organic syntheses: A case study based on the syntheses of ketene dithioacetals

Sarah C. Ball; Ian Cragg-Hine; Matthew G. Davidson; Robert P. Davies; Paul R. Raithby; Ronald Snaith

doi:10.1039/cc9960001581

The mechanisms of dilithiation reactions in organic syntheses: A case study based on the syntheses of ketene dithioacetals

Sarah C. Ball, Ian Cragg-Hine, Matthew G. Davidson, Robert P. Davies, Paul R. Raithby, Ronald Snaith

University of Cambridge

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

17 Citations (SciVal)

Abstract

An investigation of the lithiation and CS₂-insertion reactions of R¹R²CH₂ precursors (reactions used in the syntheses of ketene dithioacetals) leads to the crystal structure determination of the monolithiated complexes R¹R²CHCS₂Li·TMEDA, 3 (R¹ = Ph, R² = pyridyl) and 4 (R¹ = H, R² = 2-methylpyrazine); attempted second lithiation of 3 fails to give the R¹R²C=CS₂Li₂ species anticipated in the mechanism of reactions of this type, but synthetic and ¹H NMR spectroscopic evidence indicates that 4 can be lithiated further.

Original language	English
Pages (from-to)	1581-1582
Number of pages	2
Journal	Chemical Communications
Volume	1996
Issue number	13
DOIs	https://doi.org/10.1039/cc9960001581
Publication status	Published - 31 Dec 1996

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "The mechanisms of dilithiation reactions in organic syntheses: A case study based on the syntheses of ketene dithioacetals",

abstract = "An investigation of the lithiation and CS2-insertion reactions of R1R2CH2 precursors (reactions used in the syntheses of ketene dithioacetals) leads to the crystal structure determination of the monolithiated complexes R1R2CHCS2Li·TMEDA, 3 (R1 = Ph, R2 = pyridyl) and 4 (R1 = H, R2 = 2-methylpyrazine); attempted second lithiation of 3 fails to give the R1R2C=CS2Li2 species anticipated in the mechanism of reactions of this type, but synthetic and 1H NMR spectroscopic evidence indicates that 4 can be lithiated further.",

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T1 - The mechanisms of dilithiation reactions in organic syntheses

T2 - A case study based on the syntheses of ketene dithioacetals

AU - Ball, Sarah C.

AU - Cragg-Hine, Ian

AU - Davidson, Matthew G.

AU - Davies, Robert P.

AU - Raithby, Paul R.

AU - Snaith, Ronald

PY - 1996/12/31

Y1 - 1996/12/31

N2 - An investigation of the lithiation and CS2-insertion reactions of R1R2CH2 precursors (reactions used in the syntheses of ketene dithioacetals) leads to the crystal structure determination of the monolithiated complexes R1R2CHCS2Li·TMEDA, 3 (R1 = Ph, R2 = pyridyl) and 4 (R1 = H, R2 = 2-methylpyrazine); attempted second lithiation of 3 fails to give the R1R2C=CS2Li2 species anticipated in the mechanism of reactions of this type, but synthetic and 1H NMR spectroscopic evidence indicates that 4 can be lithiated further.

AB - An investigation of the lithiation and CS2-insertion reactions of R1R2CH2 precursors (reactions used in the syntheses of ketene dithioacetals) leads to the crystal structure determination of the monolithiated complexes R1R2CHCS2Li·TMEDA, 3 (R1 = Ph, R2 = pyridyl) and 4 (R1 = H, R2 = 2-methylpyrazine); attempted second lithiation of 3 fails to give the R1R2C=CS2Li2 species anticipated in the mechanism of reactions of this type, but synthetic and 1H NMR spectroscopic evidence indicates that 4 can be lithiated further.

UR - https://www.scopus.com/pages/publications/0012248384

U2 - 10.1039/cc9960001581

DO - 10.1039/cc9960001581

M3 - Article

AN - SCOPUS:0012248384

SN - 1359-7345

VL - 1996

SP - 1581

EP - 1582

JO - Chemical Communications

JF - Chemical Communications

IS - 13

ER -

The mechanisms of dilithiation reactions in organic syntheses: A case study based on the syntheses of ketene dithioacetals

Abstract

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