The first nonthiolic, odorless 1,3-propanedithiol equivalent and its application in thioacetalization.
2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier-Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79-97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.
Liu
Qun
Q
Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. China. liuqun@nenu.edu.cn
Che
Guangbo
G
Yu
Haifeng
H
Liu
Yingchun
Y
Zhang
Jingping
J
Zhang
Qian
Q
Dong
Dewen
D