Diborane (4) derivatives via coupling of amine monobromocyanoboranes: Study of the bromination of amine cyanoborane and molecular structures of the amine dibromocyanoboranes

Khuloud Takrouri, Eli Shalom, Israel Goldberg, Jehoshua Katzhendler, Morris Srebnik

Research output: Contribution to journalArticlepeer-review

Abstract

The first examples of diborane (4) compounds derived from amine cyanoboranes are described. A series of monobromo derivatives of amine cyanoboranes (A:BHBrCN), and dibromo derivatives (A:BBr2CN), 1-7, were prepared. Lithiation of the monobromo derivative of trimethylamine cyanoborane, using n-BuLi, did not produce the C-lithiated intermediate Li + [CH2NMe2BHBrCN]-, but instead the B-lithiated intermediate Li+ [Me3NBHCN]-, was obtained. This intermediate, when allowed to react for 16 h, coupled with the un-lithiated trimethylamine monobromocyanoborane (Me3NBHBrCN) and resulted in diborane (4) derivative formation as the 2LiBr complex. The same result was obtained when one equiv of the trimethylamine monobromocyanoborane was added to the reaction mixture 1 h after lithiation. Following the same procedure, novel diborane (4) derivatives of amine cyanoboranes were successfully obtained, 8-11, as their 2LiBr complexes from the monobromo derivatives of the corresponding amine cyanoboranes. Molecular structures of the trimethylamine dibromocyanoborane, 6, and the triethylamine dibromocyanoborane, 7, were determined using X-ray crystallography.

Original languageEnglish
Pages (from-to)4150-4158
Number of pages9
JournalJournal of Organometallic Chemistry
Volume690
Issue number18
DOIs
StatePublished - 15 Sep 2005

Keywords

  • Amine dibromocyanoboranes
  • Amine monobromocyanoboranes
  • B-B bond formation
  • B-lithiation
  • Crystal structures
  • Diboron (4) compounds

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