- 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
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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.
- Norén, Rolf
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- Solid-phase organic synthesis of aryl vinyl ethers using sulfone-linking strategy
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A novel facile solid-phase organic synthesis of aryl vinyl ethers by reaction of polystyrene-supported 2-phenylsulfonylethanol with phenols under Mitsunobu conditions and subsequent elimination reaction with DBU has been developed. The advantages of this method include straightforward operation, good yield and high purity of the products. Alternatively, a typical example of Suzuki coupling reaction on-resin was further applied to prepare 4-phenylphenyl vinyl ether for extending this method.
- Yu, Lamei,Tang, Ni,Sheng, Shouri,Chen, Rubing,Liu, Xiaoling,Cai, Mingzhong
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experimental part
p. 1027 - 1030
(2012/07/28)
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- Solid-Phase synthesis of aryl vinyl ethers based on polystyrenesupported aβ-phenylselenoethanol
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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
- Zhang, Jia-Li,Sheng, Shou-Ri,Liub, Xue,Lin, Shu-Ying
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experimental part
p. 287 - 289
(2010/02/28)
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- β-Phenylselenoethanol, an efficient reagent for the one-pot synthesis of aryl vinyl ethers
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β-Phenylselenoethanol was treated with phenols under Mitsunobu conditions and subsequent oxidation-elimination with 30% hydrogen peroxide furnished aryl vinyl ethers with good yields (85-90%) in a one-pot, two-step transformation.
- Fu, Gui-Yun,Yu, La-Mei,Mao, Xue-Chun,Wu, Dan
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experimental part
p. 595 - 597
(2009/10/15)
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- Polymer-supported β-bromoethyl selenide: An efficient reagent for the synthesis of aryl vinyl ethers
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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.
- Sheng, Shou-Ri,Liu, Xiao-Ling,Wang, Xing-Cong,Xin, Qin,Song, Cai-Sheng
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p. 2833 - 2836
(2007/10/03)
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- Acetals as New 2′-O-Protecting Functions for the Synthesis of Oligoribonucleotides: Synthesis of Uridine Building Blocks and Evaluation of Their Relative Acid Stability
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A broad variety of new acyclic vinyl ethers (see 6-41) have been synthesized via the vinyl-interchange reaction of ethyl vinyl ether at room temperature using mercury(II) trifluoroacetate as a highly efficient catalyst. The appropriate vinyl ethers were r
- Matysiak, Stefan,Fitznar, Hans-Peter,Schnell, Ralf,Pfleiderer, Wolfgang
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p. 1545 - 1566
(2007/10/03)
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- Acyl ureas, insecticides containing these compounds as well as methods for their production
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New acyl urea of the general formula STR1 in which R1 is halogen or C1 -C6 -alkyl, R2 is hydrogen or halogen, R3 is hydrogen, halogen or methyl, R4 is hydrogen, halogen or methyl, and Rsub
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- MECHANISM OF THE TRANSVINYLATION OF ALCOHOLS WITH VINYL ACETATE
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The mechanism of the transvinylation of alcohols with vinyl acetate in the presence of catalysts was studied.It includes the formation of an intermediate organomercury compound and its decomposition into the vinyl ether in the vinyl acetate medium in the presence of a mineral acid.
- Gareev, G. A.
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