page_title: Triazabicyclodecene
hierarchical_section_title: Triazabicyclodecene
caption_attribution_description: Deprotonation of C-acid by TBD N-base
context_page_description: Triazabicyclodecene is a commercially available bicyclic strong guanidine base. TBD is an organic soluble base that has been used effectively for a variety of base-mediated organic transformations such as:
  Michael reactions,
  Henry,
  Wittig reactions,
  Horner–Wadsworth–Emmons reactions,
  transesterification reactions,
  etherifications,
  ring-opening polymerizations,
  tautomerizations and epimerizations
  P–C and P–N bond formations,
  Knoevenagel condensations,
  deprotonation reactions of phenols, carboxylic acids and C-acids,
  aminolysis of esters.
  It is also known in deprotonated form, often as a ligand, for instance in Ditungsten tetra
context_section_description: Triazabicyclodecene (1,5,7-Triazabicyclo[4.4.0]dec-5-ene or TBD) is a commercially available bicyclic strong guanidine base (pKₐ = 25.98 in CH₃CN and pKₐ = 21.00 in THF). TBD is an organic soluble base that has been used effectively for a variety of base-mediated organic transformations such as:
  Michael reactions,
  Henry (nitroaldol reactions),
  Wittig reactions,
  Horner–Wadsworth–Emmons reactions,
  transesterification reactions,
  etherifications,
  ring-opening polymerizations (Scheme 1),
  tautomerizations and epimerizations
  P–C and P–N bond formations,
  Knoevenagel condensations,
  deprotonation reactions of phenols, carboxylic acids and C-acids (Scheme 2),
  aminolysis of esters.
  It is also known in deprotonated form (at the 7-position), often as a ligand, for instance in Ditungsten tetra(hpp)
caption: Scheme 2. Deprotonation of C–H acid. TBD can be considered as a very interesting agent for studies of the proton transfer reaction reactions and formation of the hydrogen-bonded chains with phenols and C–H acids.[8]
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