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Direct Transformation of Propargylic Alcohols and O,O-Diethyl Phosphorothioic Acid into S-(2H-Chromen-4-yl) Phosphorothioates
Synthesis ( IF 2.6 ) Pub Date : 2019-11-14 , DOI: 10.1055/s-0039-1690749
Xian-Rong Song , Tao Yang , Haixin Ding , Qiang Xiao 1
Affiliation  

An environmentally benign and efficient method has been successfully developed to generate S-(2H-chromen-4-yl) phosphorothioates from easily available 2-(3-hydroxyprop-1-ynyl)phenols and O,O-diethyl phosphorothioic acid [(EtO)2P(O)SH] with water as the only byproduct. The reaction proceeds smoothly in moderate to excellent yields. It is noted that (EtO)2P(O)SH acts not only as an acid promoter, but also as the nucleophile to attack the allenic carbocation intermediate.

中文翻译:

炔丙醇和O,O-二乙基硫代磷酸直接转化为S-(2H-Chromen-4-yl)硫代磷酸酯

环境友好和有效的方法已被成功地开发,以产生小号- (2- ħ -苯并吡喃-4-基)从容易获得的硫代磷酸酯2-(3-羟基丙-1-炔基)苯酚和øö -二乙基硫代磷酸[( EtO)2 P(O)SH],唯一的副产物是水。反应平稳进行,产率中等至优异。注意,(EtO)2 P(O)SH不仅起酸促进剂的作用,而且还作为亲核试剂攻击烯丙基碳正离子中间体。
更新日期:2019-11-15
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