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首页> 外文期刊>Chemistry: A European journal >Exploring the Reactivity of alpha-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited
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Exploring the Reactivity of alpha-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited

机译：探索α-锂化的芳基苄基醚的反应性：抑制[1,2]-维蒂希重排和重新提出的机制建议。

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摘要

By carefully controlling the reaction temperature, treatment of aryl benzyl ethers with tBuLi selectively leads to alpha-lithiation, generating stable organolithiums that can be directly trapped with a variety of selected electrophiles, before they can undergo the expected [1,2]-Wittig rearrangement. This rearrangement has been deeply studied, both experimentally and computationally, with aryl alpha-lithiated benzyl ethers bearing different substituents at the aryl ring. The obtained results support the competence of a concerted anionic intramolecular addition/elimination sequence and a radical dissociation/recombination sequence for explaining the tendency of migration for aryl groups. The more favored rearrangements are found for substrates with electron-poor aryl groups that favor the anionic pathway.
机译：通过仔细控制反应温度，用tBuLi处理芳基苄基醚有选择地导致α-锂化，生成稳定的有机锂，这些有机锂可直接被多种选定的亲电试剂捕获，然后再进行预期的[1,2] -Wittig重排。对于这种重排已经在实验和计算上进行了深入研究，用在芳基环上带有不同取代基的芳基α-锂化的苄基醚。获得的结果支持了协同的阴离子分子内添加/消除序列和自由基解离/重组序列的能力，以解释芳基迁移的趋势。对于具有有利于阴离子途径的贫电子芳基的底物，发现了更有利的重排。

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