64283-03-0Relevant articles and documents
Synthesis of α-aliphatic and β-aromatic substituted taurines via regioselective ring opening of thiiranes with ammonia
Yu, Hao,Cao, Shengli,Zhang, Leilei,Liu, Gang,Xu, Jiaxi
experimental part, p. 2205 - 2209 (2010/02/27)
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 on their more substituted ring carbon atoms. The current method is an effective and atom-economic route for the synthesis of mono- and disubstituted α-alkyl-and β-aryl-substituted taurines. Georg Thieme Verlag Stuttgart.
