烯烃与双（三氟基）乙烯反应中的溶剂效应

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI:10.1002/ajoc.202400651

Dr. Hikaru Yanai , Reon Sano , Dr. Shoki Hoshikawa , Prof. Dr. Takashi Matsumoto

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引用次数: 0

摘要

几种烯烃与Tf2C=CH2 （Tf=CF3SO2）反应时的反应模式由反应溶剂控制。例如，虽然与烯丙基硅烷的反应在MeCN中选择性地产生正常的烯丙基化产物，但在甲苯中形成gem-bis（三氟基）环戊烷。特别是，（3+2）环加合物的选择性形成是通过使用位阻烯丙基硅烷实现的。我们还发现在与简单烯烃的反应中有明显的溶剂效应。也就是说，在热甲苯中，烯烃与Tf2C=CH2的Alder烯反应顺利进行，得到相应的带有超酸性二（三氟基）甲基的(E)-烯烃。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Solvent Effects in the Reactions of Alkenes with gem‐Bis(triflyl)ethylene

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Solvent Effects in the Reactions of Alkenes with gem‐Bis(triflyl)ethylene

The reaction modes in the reactions of several alkenes with Tf₂C=CH₂ (Tf=CF₃SO₂) have been controlled by the reaction solvents. For example, although the reaction with allylsilanes selectively produced normal allylation products in MeCN, gem‐bis(triflyl)cyclopentanes were formed in toluene. In particular, a selective formation of the (3+2) cycloadducts was achieved by using sterically hindered allylsilanes. We also found notable solvent effects in the reaction with simple alkenic hydrocarbons. That is, in hot toluene, the Alder ene reaction of the alkenes with Tf₂C=CH₂ smoothly proceeded to give the corresponding (E)‐alkenes bearing a superacidic bis(triflyl)methyl group.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.