Oxidation of E,E‐bis(3‐bromo‐1‐chloro‐1‐propen‐2‐yl) chalcogenides and use of E,E‐bis(3‐bromo‐1‐chloro‐1‐propen‐2‐yl)sulfone in heterocyclization with primary amines

Oxidation of E,E‐bis(3‐bromo‐1‐chloro‐1‐propen‐2‐yl) sulfide and selenide with hydrogen peroxide in chloroform/acetic acid or acetic acid affords previously unknown E,E‐bis(3‐bromo‐1‐chloro‐1‐propen‐2‐yl) sulfoxide, selenoxide, and sulfone. The reaction of E,E‐bis(3‐bromo‐1‐chloro‐1‐propen‐2‐yl) sulfone with primary amines in ethanol in the presence of NaHCO₃ or Na₂CO₃ is found to lead not only to heterocyclization but also to alcoholysis of the chloromethylidene groups in the intermediate bis(chloromethylidene) derivatives of thiomorpholine‐1,1‐dioxides to afford N‐organyl‐2(E),6(E)‐bis(ethoxymethylidene) thiomorpholine‐1,1‐dioxides as final products.