Abstract
The rates of base-catalysed hydrogen-isotope exchange reactions of various sulphides and their corresponding oxygen analogues have been measured in order to compare the relative acidifying effects of mercapto and alkoxy groups toward α-hydrogen atoms. Practically no exchange reaction was abserved in the oxygen compounds, whereas, with the sulphur compounds, the reaction readily takes place, the rate being increased several powers of ten by the substitution of one additional mercapto group. Furthermore, dramatic rate increase was observed when an open chain compound, orthothioformate was cyclized to the corresponding bicyclic compound. These observations are interpreted in terms of the 3d orbital resonance of the sulphur atom.
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