38648-75-8Relevant articles and documents
Reactions of thioesters with organic azides - A novel access to imidates and thioimidates
Mloston,Romanski,Heimgartner
, p. 975 - 982 (2007/10/03)
The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110°C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the "twofold extrusion" of N2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.
