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[摘要]：Thiiranes are important starting materials for the synthesis of substituted taurines. The regioselectivity of ring-opening reactions of thiiranes with ammonia in the presence of silver nitrate was investigated. The results of the ring-opening reaction and subsequent peroxy acid oxidation indicate that alkyl-substituted thiiranes give rise to 1-monoalkyl- and 1,1-dialkyltaurines, whereas aryl-substituted thiiranes produce 2-aryl-, 2-alkyl-2-aryl-, and 2,2-diaryltaurines. This shows that alkyl-substituted thiiranes were attacked on their less-substituted ring carbon atoms, while aryl-substituted thiiranes were attacked oil their more substituted ring carbon atoms. The current method is all effective and atom-economic route for the synthesis of mono- and disubstituted alpha-alkyl- and beta-aryl-substituted taurines. |
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