New Reactions of Sulfur-Centered 1,3-Dipoles Generated from Thioketones in Three-Component Reactions with Phenyl Azide and an Electron-Deficient Dipolarophile

ABSTRACT:

Reactions of cycloaliphatic thioketones with phenyl azide in the presence of an electron-deficient C-C-dipolarophile have been studied. It was shown that the course of the reactions and the structures of the products depend strongly on the type of the dipolarophile used. Only in the case of fumaronitrile the interception product of the intermediate thiocarbonyl-S-imide was obtained.

KEY WORDS::

• thioketones
• thiocarbonyl-S-imides
• thiocarbonyl-S-ylides
• 1,3-dipolar cycloaddition
• 1,5-electrocyclization