Abstract
AbstractIn aqueous solutions at 100°C varying from HCl 2N to NaOH 2N, N‐phenylthiocarbamoyl derivatives of aminoalkylsulfuric monoesters C6H5NHCSROSO3H are split in the following ways: With R = CH2CH(CH3) or (CH2)3the scission of the monoester group is very rapid in the hole pH‐range studied, especially in alkaline medium; the resulting cyclic products, 5‐methyl‐2‐phenylamino‐thiazoline and 2‐phenylimino‐tetrahydrothiazine respectively, formed by nucleophilic attack of an unshared pair of the S atom on the C bearing the monoester group, have been isolated and identified. With R = (CH2)4, the rate of the scission in alkaline or neutral medium is very much higher than that of an alkylsulfuric monoester; in these media a cyclic product is also formed (this time by nucleophilic attack of the unshared pair of the thiocarbamoylated N atom on the C bearing the monoester function) which has been isolated after alcaline scission, and identified as N‐phenylcarbomoyl‐pyrrolidine. In acid medium, no special influence of the phenylthiocarbamoyl group is observed. With R = (CH2)5 or (CH2)6, the rate of the scission in alkaline medium is 30 to 1000 times lower than in the previous cases; no pure organic scission products have been isolated. In acid or neutral medium, these two esters behave like usual alkylsulfuric acids.
Published Version
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