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Strong Organic Bases

MTBD (1) and TBD (2) are bicyclic guanidine organic bases. The pKa values of the conjugate acids of these bases in acetonitrile are 25 and 26, respectively.1) 1 and 2 show relatively strong basicities comparing to DBU and TMG (tetramethylguanidine), which are well known as organic bases.
1. Selective Deprotonation of Sulfonamide2a)
2. Aziridine Ring-Opening Reaction2b)
Instead of DBU and CuOAc, the use of 2 as a base gives better yields (59% to 78%).
3. Wittig, Horner–Emmons Reactions3)
In many cases, the reactions are carried out without anhydrous and inert conditions.


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