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Triazabicyclodecene
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Triazabicyclodecene : ウィキペディア英語版
Triazabicyclodecene

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Triazabicyclodecene (1,5,7-Triazabicyclo()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 which has been used effectively for a variety of base-mediated organic transformations such as:〔Adam Huczynski, Bogumil Brzezinski, "1,5,7-Triazabicyclo()dec-5-ene", e-EROS Encyclopedia of Reagents for Organic Synthesis,John Wiley & Sons, Ltd 2008,〕
* 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,〔Cyrille Sabot, Kanduluru Ananda Kumar, Stéphane Meunier, Charles Mioskowski, "A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo()dec-5-ene (TBD) under solvent-free conditions", Tetrahedron Lett., 2007, 3863-3866 〕
It is also known in deprotonated form (at the 7-position), often as a ligand, for instance in Ditungsten tetra(hpp)
==References==


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