Triphenylpyridinium ylid 2, generated by the decarboxylation of betaine 1, were noted to react with acetyl chloride, chloroform or acetone to form addition-elimination product and proton extraction - carbanion addition products, respectively. The reaction with chloroform was determined as pseudo first order from kinetic experiments. The values of kobsd and t1/2 for decarboxylation at 20, 40 and 50C were calculated to be 4.6 x 10-4, 8.8 x 10-3, 2.8 x 10-2 min-1 and 1.5 x 103, 78, 24 minutes, respectively.
Several cyclic amino acids (1-4) were synthesized from glycine. Isocyanate ester was prepared as the key intermediate and reacted with dibromoalkanes to afford the target compounds.
The reactions of triphenylpyrylium salt 1 with various anuno acids were explored and compared. The reactions with most α-amino acids yielded decarboxylation products 2 via decarboxylation. The reactions with glutamic acid, lysine and ACC (1-aminocyclopropyl-carboxylic acid) gave triphenylpyndine 8, dimer 9 and acid 5a-acc, respectively. The reactions with βand γ-amino acids yielded triphenylpyridine by intramolecular elinunation.
