A hierarchy of aryloxide deprotection by boron tribromide
A hierarchy of aryloxide deprotection by boron tribromide
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DOI：
10.1021/ol0489898
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发表时间：
2004-08-05
期刊：
影响因子：
5.2
通讯作者：
Finn, MG
中科院分区：
文献类型：
--
作者：
Punna, S;Meunier, S;Finn, MG
芳基炔丙基醚和酯在芳基甲基醚和酯的存在下被三溴化硼在二氯甲烷中选择性裂解。在相同条件下，烯丙基醚发生非常快速的克莱森重排，苄基醚也比炔丙基裂解得更快。提出了一种分子内传递溴的炔丙基末端的机制。
Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed.