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Triazabicyclodecene



Triazabicyclodecene or 1,5,7-Triazabicyclo[4.4.0]dec-5-ene or TBD C7H13N3 is an organic compound and a guanidine. it is used in organic chemistry as a catalyst. The compound is strongly basic with a pKa of the conjugate acid of 26. It has been used as a catalyst in Michael reactions, Wittig reactions, Henry reactions and in transesterification.

In one study [1] TBD is used as a catalyst in the ring opening polymerization of caprolactone to polycaprolactone (Scheme 1 1). TBD acts as a bifunctional catalyst with simultaneous acyl transfer and hydrogen bonding.

The compound is structurally related to DBU.

References

  1. ^  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
  2. ^ Scheme 1. 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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Triazabicyclodecene". A list of authors is available in Wikipedia.
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