The Bonding and Reactivity of α-Carbonyl Cyclopropanes,Synthesis

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The Bonding and Reactivity of α-Carbonyl Cyclopropanes
Synthesis ( IF 2.2 ) Pub Date : 2019-10-01 , DOI: 10.1055/s-0039-1690695
Alexander J. Craig , Bill C. Hawkins ₁

Affiliation

The cyclopropane functionality has been exploited in a myriad of settings that range from total synthesis and methodological chemistry, to medical and materials science. While it has been seen in such a breadth of settings, the typical view of the cyclopropane moiety is that its reactivity is derived primarily from the release of ring strain. While this simplified view is a useful shorthand, it ignores the specific nature of cyclopropyl molecular orbitals. This review aims to present the different facets of cyclopropane bonding by examining the main models that have been used to explain the reactivity of the functionality over the years. However, even with advanced theory, being able to precisely predict the reactivity of an exact system is nigh impossible. Specifically chosen, carbonyl-bearing cyclopropyl species act as so-called acceptor cyclopropanes and, if correctly derivatised, donor–acceptor cyclopropanes. By undertaking a case study of the history of carbonyl cyclopropanes in organic synthesis, this review highlights the relationship between the understanding of theory and pattern recognition in developing new synthetic methods and showcases those successful in balancing this critical junction.

中文翻译：

α-羰基环丙烷的键合和反应活性

从全合成和方法化学到医学和材料科学，无数种环境都利用了环丙烷的功能。尽管已经在如此广泛的环境中看到了，但是环丙烷部分的典型观点是其反应性主要源自环应变的释放。尽管此简化视图是一个有用的速记，但它忽略了环丙基分子轨道的特殊性质。这篇综述旨在通过考察多年来用来解释功能性反应性的主要模型，介绍环丙烷键合的不同方面。但是，即使采用先进的理论，也几乎不可能精确预测精确系统的反应性。专门选择的含羰基的环丙基物质起所谓的受体环丙烷的作用，如果正确衍生，则起供体-受体环丙烷的作用。通过对有机合成中羰基环丙烷的历史进行个案研究，本综述重点介绍了在开发新的合成方法中理论理解与模式识别之间的关系，并展示了成功地平衡该关键连接的方法。

更新日期：2019-10-02

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