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

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)1581-1582
Number of pages2
JournalChemical Communications
Volume1996
Issue number13
DOIs
Publication statusPublished - 31 Dec 1996

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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