Generation and reactions of overcrowded diaryldilithiostannane and diaryldipotassiostannane

Tomoyuki Tajima, Nobuhiro Takeda, Takahiro Sasamori, Norihiro Tokitoh

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Exhaustive reduction of an overcrowded dibromostannane bearing two bulky aromatic substituents, Tbt(Dip)SnBr2 {Tbt = 2,4,6- tris[bis(trimethylsilyl)methyl]phenyl; Dip = 2,6-diisopropylphenyl}, with an excess amount of lithium naphthalenide in THF at -78°C gave the corresponding dilithiostannane, Tbt(Dip)SnLi2, the generation of which was confirmed by trapping experiments with some electrophiles together with 119Sn and 7Li NMR spectroscopy. The diaryldilithiostannane was found to be stable in solution under an inert gas below -25°C. The potassium analogue, Tbt(Dip)-SnK2, was also generated by the reduction of the dibromostannane in THF at -78°C by the use of KC8 as a reductant. The reactions of dilithiostannane and dipotassiostannane obtained with o-dibromobenzene did not give a stannacyclopropabenzene derivative but an unexpected cyclization product, a stannacyclobutabenzene derivative, in contrast to the reactions of the corresponding dilithiosilane and dilithiogermane, Tbt(Dip)ELi2 (E = Si, Ge), with o-dibromobenzene leading to the formation of the corresponding metallacyclopropabenzenes as stable crystalline compounds. A preliminary result of the synthesis of a tin-tellurium double-bond compound from the dilithiostannane is also presented.

Original languageEnglish
Pages (from-to)4291-4300
Number of pages10
JournalEuropean Journal of Inorganic Chemistry
Issue number21
DOIs
Publication statusPublished - Nov 4 2005
Externally publishedYes

Fingerprint

Bearings (structural)
Tellurium
Derivatives
Noble Gases
Tin
Cyclization
Reducing Agents
Lithium
Nuclear magnetic resonance spectroscopy
Potassium
Crystalline materials
Experiments
1,2-dibromobenzene

Keywords

  • Anions
  • Group 14 elements
  • Lithium
  • Potassium
  • Solid-state structures
  • Tin

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Generation and reactions of overcrowded diaryldilithiostannane and diaryldipotassiostannane. / Tajima, Tomoyuki; Takeda, Nobuhiro; Sasamori, Takahiro; Tokitoh, Norihiro.

In: European Journal of Inorganic Chemistry, No. 21, 04.11.2005, p. 4291-4300.

Research output: Contribution to journalArticle

Tajima, Tomoyuki ; Takeda, Nobuhiro ; Sasamori, Takahiro ; Tokitoh, Norihiro. / Generation and reactions of overcrowded diaryldilithiostannane and diaryldipotassiostannane. In: European Journal of Inorganic Chemistry. 2005 ; No. 21. pp. 4291-4300.
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