Triazabicyclodecene

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Structure of TBD
Structure of TBD
3-D structure of TBD
3-D structure of TBD

Triazabicyclodecene (1,5,7-Triazabicyclo[4.4.0]dec-5-ene - TBD, C7H13N3). TBD is the commercially available bicyclic strong guanidine base (pKa = 25.98 in CH3CN and pKa = 21.00 in THF). TBD is an organic soluble base which has been used effectively for a variety of base-mediated organic transformations such as[1]:

Scheme 1. Caprolactone polymerization. TBD is used as a catalyst in the ring opening polymerization of caprolactone to polycaprolactone. TBD acts as a bifunctional catalyst with simultaneous acyl transfer and hydrogen bonding .
Scheme 1. Caprolactone polymerization. TBD is used as a catalyst in the ring opening polymerization of caprolactone to polycaprolactone. TBD acts as a bifunctional catalyst with simultaneous acyl transfer and hydrogen bonding[2] [3].
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.
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.[4]


[edit] References

  1. ^ Adam Huczynski, Bogumil Brzezinski, "1,5,7-Triazabicyclo[4.4.0]dec-5-ene", e-EROS Encyclopedia of Reagents for Organic Synthesis,John Wiley & Sons, Ltd 2008,doi:10.1002/047084289X.rn00786
  2. ^ Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters Russell C. Pratt, Bas G. G. Lohmeijer, David A. Long, Robert M. Waymouth, and James L. Hedrick J. Am. Chem. Soc.; 2006; 128(14) pp 4556 - 4557 Abstract
  3. ^ Reaction specs: initiator 4-pyrenebutanol (pyrene enables end-group determination by [[UV/VIS spectroscopy) and monomer caprolactone added in ratio 1:100 , targeted degree of polymerization = 100, with TBD cat. 0.5% in benzene 72% conversion in 8 hours. polydispersity index 1.16
  4. ^ A. Huczyński, I. Binkowska, A. Jarczewski, B. Brzezinski, "Spectroscopic studies of the 1:1 complexes of 4-nitrophenyl(bis(ethylsulfonyl))methane and phenyl(bis(ethylsulfonyl))methane with 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene and 1,5,7-triazabicyclo(4.4.0)dec-5-ene", Journal of Molecular Structure, 841(1-3), 2007, 133-136, doi:10.1016/j.molstruc.2007.01.005
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