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Thorpe-Ingold效应及其在有机成环反应中的应用
Thorpe-Ingold Effect and Its Application in Cyclizations in Organic Chemistry
本文首先介绍了Thorpe-Ingold效应及其相关理论和实验研究进展，然后综述了近年来Thorpe-Ingold效应在形成三、四、五和六元环产物的环化反应中的应用。Thorpe-Ingold效应可以有效地促进分子内和分子间环化，提高环化的产率和速率。该效应主要通过空间效应、电子效应或者两者协同起作用，在某些情况下，该效应还会受催化剂和溶剂等影响。利用该效应可以促使一些难以发生的环化反应顺利进行，并能获得较好的产率。
The Thorpe-Ingold effect and its advances in both theoretical and experimental studies are introduced briefly. Its recent applications in cyclizations for formations of three-, four-, five-, and six-membered ring products are reviewed. The Thorpe-Ingold effect can promote intra- and intermolecular cyclizations effectively, accelerating reaction rates and improving yields in cyclizations. The effect exerts its influence in reactions through steric hindrance and/or electronic effect and is impacted by catalysts and solvents in some cases. Application of the effect can help some difficult cyclization reactions to occur smoothly, affording the desired products in good yields.
Contents
1 Thorpe-Ingold effect
2 Application in cyclizations involving formations of three-membered ring products
2.1 Cyclopropane derivatives
2.2 Ethylene oxide derivatives
3 Application in cyclizations involving formations of four-membered ring products
3.1 Cyclobutane deivatives
3.2 Oxacyclobutane derivatives
4 Application in cyclizations involving formations of five-membered ring products
4.1 Cyclopentane derivatives
4.2 Azacyclopentane derivatives
4.3 Oxacyclopentane derivatives
4.4 Thiazolidine derivatives
4.5 Phosphacyclopentane derivatives
4.6 Silicacyclopentane derivatives
5 Application in cyclizations involving formations of six-membered ring products
5.1 Cyclohexane derivatives
5.2 Azacyclohexane derivatives
5.3 Oxacyclohexane derivatives
5.4 Silicacyclohexane derivatives
6 Miscellaneous
7 Summary and prospects
Thorpe-Ingold效应
Thorpe-Ingold effect
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