940-14-7Relevant articles and documents
Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids
Norén, Rolf
, (2021/04/07)
A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.
Solid-Phase synthesis of aryl vinyl ethers based on polystyrenesupported aβ-phenylselenoethanol
Zhang, Jia-Li,Sheng, Shou-Ri,Liub, Xue,Lin, Shu-Ying
experimental part, p. 287 - 289 (2010/02/28)
A novel facile solid-phase organic synthesis of aryl vinyl ethers by reaction of polystyrene-supported β-phenylselenoethanol with phenols under Mitsunobu conditions and subsequent oxidation-elimination with 30% hydrogen peroxide has been developed. The ad
Polymer-supported β-bromoethyl selenide: An efficient reagent for the synthesis of aryl vinyl ethers
Sheng, Shou-Ri,Liu, Xiao-Ling,Wang, Xing-Cong,Xin, Qin,Song, Cai-Sheng
, p. 2833 - 2836 (2007/10/03)
A simple and efficient procedure for the solid-phase synthesis of aryl vinyl ethers using polymer-supported β-bromoethyl selenide with traceless linker strategy is described.