Abstract
A detailed study was carried out on the decomposition of dibenzothiophene dioxide in the presence of both sodium and potassium hydroxide at 200–300°. Our results show that the stability of the dibenzothiophene nucleus is markedly dependent on the oxidation state of the S-atom. The products formed in the decomposition reaction vary with temperature, contact time, and the initial ratio of base to dioxide. In the presence of excess base at 300°, dibenzothiophene dioxide was converted to dibenzofuran in high yield. The formation of the furan apparently proceeds by a multistep reaction sequence in which 2-phenylbenzene sulfonic acid and 2-phenylphenol are unstable intermediates. We also investigated the decomposition of dibenzothiophene monoxide, benzothiophene dioxide, n-octyl sulfoxide and sulfone, and diphenyl sulfoxide and sulfone under these conditions. The aliphatic S-derivatives decomposed by a typical beta-elimination reaction. The products formed from the other oxidized S-derivatives suggest that the decomposition process involves a complex series of addition, cleavage, and elimination reactions.
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