Triazabicyclodecene Explained

Triazabicyclodecene (1,5,7-triazabicyclo[4.4.0]dec-5-ene or TBD) is an organic compound consisting of a bicyclic guanidine. For a charge-neutral compound, it is a relatively strong base that is effective for a variety of organic transformations. TBD is colorless solid that is soluble in a variety of solvents.^[1]

Reactivity

As a strong base, TBD fully deprotonates most phenols, carboxylic acids, and some C-acids.^[2] It catalyzes a variety of reactions including Michael reactions, Henry reactions (nitroaldol reactions), transesterification reactions, and Knoevenagel condensations.^[3]

Deprotonation at the 7-position gives a particularly electron-rich ligand as manifested in the redox properties of ditungsten tetra(hpp).

See also

• 1,8-Diazabicyclo(5.4.0)undec-7-ene, a structurally related strong base
• 7-Methyl-TBD, a methyl derivative of TBD

Notes and References

1. Encyclopedia: 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. 2008. 10.1002/047084289X.rn00786. 978-0-471-93623-7.
2. 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. J. Mol. Struct.. 841. 1–3. 2007. 133–136. 10.1016/j.molstruc.2007.01.005. 2007JMoSt.841..133H .
3. Cyrille. Sabot. Kanduluru Ananda. Kumar. Stéphane. Meunier. Charles. Mioskowski. A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions. Tetrahedron Lett.. 2007. 48. 22. 3863–3866. 10.1016/j.tetlet.2007.03.146.