Triazabicyclodecene

Updated on Jan 11, 2024

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Formula C7H13N3 ChemSpider 72164		Molar mass 139.2 g/mol Pubchem 79873

Melting point 125 to 130 °C (257 to 266 °F; 398 to 403 K)

Triazabicyclodecene (1,5,7-Triazabicyclo[4.4.0]dec-5-ene or TBD) is a commercially available bicyclic strong guanidine base (pK_a = 25.98 in CH₃CN and pK_a = 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:

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)

References

Triazabicyclodecene Wikipedia

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