Chemoselective Thioacetalization Using 3-(1,3-Dithian-2-ylidene)pentane-2,4-dione as an Odorless and Efficient Propane-1,3-dithiol Equivalent under Solvent-Free Conditions
Yan Ouyang, Dewen Dong*, Chunbai Zheng, Haifeng Yu, Qun Liu, Zhenqian Fu
*Department of Chemistry, Northeast Normal University, Changchun, 130024, P.
R. of China, Email: dongdw663
nenu.edu.cn
Y. Ouyang, D. Dong, C. Zheng, H. Yu, Q. Liu, Z. Fu, Synthesis, 2006, 3801-3804.
DOI: 10.1055/s-2006-950298
Abstract
As a non-thiolic, odorless propane-1,3-dithiol equivalent, 3-(1,3-dithian-2-ylidene)pentane-2,4-dione has been investigated in acid-promoted thioacetalization under solvent-free conditions. A range of selected aldehydes and aliphatic ketones have been converted into the corresponding dithioacetals in high yields. The relatively slow reaction rate of aromatic ketones allows chemoselective protection.
see article for more examples
D. Dong, Y. Ouyang, H. Yu, Q. Liu, J. Liu, M. Wang, J. Zhu, J. Org. Chem., 2005, 70, 4535-4537.
Key Words
chemoselectivity, concentrated hydrochloric acid, solvent-free reaction, thioacetalization, α-oxo ketene S,S-acetals, 1,3-dithianes, thioacetalization
ID: J66-Y2006-3790
