对乙烯基环氧化物添加的二甲:对SN2和SN2'分流体进行绝缘控制
Amos B Smith1, Suresh M Pitram, Matthew J Gaunt
1Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia Pennsylvania 19104, USA. smithab@sas.upenn.edu
迪离子中的固体阻碍控制了与乙烯基环氧化物反应的化学选择性. 不受阻的离子产生SN2产物,而受阻的离子产生SN2产物.
科学领域:
- 有机化学 有机化学
- 立体选择性合成 立体选择性合成
背景情况:
- 乙烯基环氧化物是多功能合成中间体.
- 二甲离子是有机合成中有用的核.
研究的目的:
- 为了研究二甲离子添加到乙烯酸环氧化物中的立体化学结果.
- 探索二甲替代物固醇对反应选择性的影响.
主要方法:
- 二甲离子与乙烯基环氧化物的反应.
- 使用立体化学方法分析反应产品.
主要成果:
- 化学选择性形成的SN2附加物与未负担的迪离子.
- 占主导地位的SN2'附加物与硬质负载的迪离子的形成.
- 在SN2'通路中增加了syn-stereospecific的添加.
结论:
- 迪替代物的固体质量是添加维нил环氧化物中的化学选择性的关键决定因素.
- 该SN2'途径以同步立体化学进行,提供可预测的立体化学控制.
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