Mechanistic Studies on Thiazolidine Formation in Aldehyde/Cysteamine Model Systems.
A mechanism was proposed to elucidate the formation of a thiazolidine in aldehyde/cysteamine model systems. Buffer dramatically promotes thiazolidine formation from formaldehyde and cysteamine. Phosphate tends to stabilize the primary carbocation formed, and this may lead to completion of the cyclization by attack of the amino nitrogen on the activated carbon. Protic solvent, by removing the water molecule, further enhances thiazolidine formation. Redox reaction catalyzed by phosphate ions results in the conversion of thiazolidine to the corresponding thiazoline through hydride transfer.
Huang
TC
Department of Food Science and Technology, National Pingtung University of Science and Technology, 912 Pingtung, Taiwan, and Department of Food Science, Rutgers University, New Brunswick, New Jersey 08903.
Huang
LZ
Ho
CT