Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles.
Starting from β-oxodithioesters and hydroxylamine, two completely different transformations afford either β-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of β-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave β-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of β-oxodithioesters and hydroxylamine in HOAc at 90 °C.
Department of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Jiaheng
J
Li
Department of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Wei
W
Ma
Department of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Wenbo
W
Ming
Department of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Cong
C
Xu
Department of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Na
N
Wei
Department of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.|State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences , Changchun 130022, P. R. China.
Mang
M
Wang