Preparation of lithium stannide mixtures in organic solvents. A alternate source of lithium in organolithium chemistry

Reuben D. Rieke, Jun Sik Lee, Young Sik Kye, Gerard Harbison

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Lithium stannides were prepared from lithium naphthalenide and tin (II) chloride or tin (0) powder in THF solvent at room temperature under dry argon atmosphere. They were characterized with elemental analysis, XRD, and solid 6.7Li NMR. Stabilities and reactivities of lithium stannides prepared from different conditions were tested and showed they were stable for a limited time at low temperatures. Best reactivity was obtained when they were prepared from tin (II) chloride and an excess of lithium naphthalenide. The lithium stannide mixture can reductively cleave carbon-halogen bonds and yield pinacol coupling with aldehydes. Organolithium compounds prepared from lithium stannides and organic halides add to ketones or aldehydes under Barbier conditions.

Original languageEnglish (US)
Pages (from-to)3421-3425
Number of pages5
JournalJournal of Organometallic Chemistry
Volume689
Issue number21
DOIs
StatePublished - Oct 15 2004

Fingerprint

Lithium
Organic solvents
stannides
lithium
chemistry
Tin
preparation
tin
Aldehydes
Chlorides
Lithium Compounds
aldehydes
reactivity
chlorides
Halogens
Temperature
Argon
Ketones
Atmosphere
Powders

Keywords

  • Li NMR
  • Lithium stannide
  • Organolithium
  • Reductive cleavage of C-X bond

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Preparation of lithium stannide mixtures in organic solvents. A alternate source of lithium in organolithium chemistry. / Rieke, Reuben D.; Lee, Jun Sik; Kye, Young Sik; Harbison, Gerard.

In: Journal of Organometallic Chemistry, Vol. 689, No. 21, 15.10.2004, p. 3421-3425.

Research output: Contribution to journalArticle

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