Reactions of 4-tosyl-2-phenyl-5-chloro-1,3-thiazole with N-, O-, and S-nucleophiles

被引:0
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作者
K. V. Turov
T. K. Vinogradova
V. S. Brovarets
B. S. Drach
机构
[1] National Academy of Sciences of Ukraine,Institute of Bioorganic Chemistry and Petrochemistry
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关键词
EtOH; NaSH; Tosylates; Thiophenol; Thiazole Ring;
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摘要
The accessible two-center electrophilic substrate 4-tosyl-2-phenyl-5-chloro-1,3-thiazole reacts regioselectively with N-, O-, and S-nucleophiles to eliminate a chloride ion. The analog of this substrate, 4-tosyl-2-phenyl-5-p-chlorophenylsulphonyl-1,3-thiazole, reacts with “soft” and “hard” nucleophiles differently: with the participation of C5 or C4 center, respectively, that seems to be caused by the principle of “symbiosis” in the transition state.
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页码:825 / 828
页数:3
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