Abstract
AbstractThe mechanism of the reaction of 4H‐3,1‐benzoxathiin‐4‐thione (3) under flash vacuum thermolysis conditions has been studied by UV‐photoelectron spectra. It was shown that in the first step of the reaction at 400° 3 underwent the Schönberg–Newman–Kwart rearrangement to give 4H‐1,3‐benzodithiin‐4‐one (6). Increasing of the temperature to 650° resulted in the elimination of thioformaldehyde and the formation of benzothiet‐2‐one (1). Subsequent elevation of the temperature prompted presumably the ring opening of 1 to (6‐thioxocyclohexa‐2,4‐dien‐1‐ylidene)methanone (7) (at 680°), which at 700° eliminated CO and underwent a Wolff‐type ring contraction to give (cyclopenta‐2,4‐dien‐1‐ylidene)methanethione (2). UV‐Photoelectron spectra were recorded at different steps of the reaction and analyzed considering the theoretical evaluation of ionization potentials.
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