Racemization of sulfinic esters with trichloroacetic anhydride |
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Authors: | Jozef Drabowicz Shigeru Oae |
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Institution: | Department of Chemistry, University of Tsukuba, Sakura-mura, Ibaraki 300-31, Japan |
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Abstract: | Both alkane- and arene-sulfinates undergo racemization and oxygen exchange reaction with trich-loroacetic anhydride. The rate of racemization of (?)menthyl (?)p-toluenesulfinate was found to be twice that of oxygen exchange, suggesting the reaction involves a Walden inversion. When reaction was carried out in benzene, the rate of racemization was found to be first order with respect to both sulfinic ester and trichloroacetic anhydride. The substituent effect is large (p = ?1.53) suggesting that the initial acylation is the rate-determining step. The rate of racemization was found to be retarded by the addition of perhaloacetic acid while very small catalytic effect of mercuric chloride was observed. |
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Keywords: | Permanent address: Department of Organic Sulfur Compounds Centre of Molecular and Macromolecular Studies Polish Academy of Sciences 90–362 ?odz Boczna 5 Poland |
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