在FLP化学中,缺电子环烯酸作为易斯酸
Dipendu Mandal1,2, Zheng-Wang Qu3, Stefan Grimme3
1Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, China.
概括
缺电子的环烯酸子表现出易斯酸性,形成添加物和挫败的易斯对 (FLP). 这些FLP可以通过添加基或去质子化来形成新的C-C键,从而扩大FLP的化学应用.
科学领域:
- 有机化学 有机化学
- 有机金属化学 有机金属化学
- 计算化学的计算化学
背景情况:
- 环烯酸,尽管存在π电子,但可以是易斯酸性.
- 缺电子的替代剂增强了环烯酸的易斯酸度.
研究的目的:
- 用电子缺陷替代剂研究环烯酸的易斯酸度.
- 探索这些离子与素的反应性,包括挫败的易斯对 (FLP) 的形成.
- 证明FLP化学在涉及非局部化π-的反应中的应用.
主要方法:
- 对化物和电子亲和力的计算检查.
- 用素对易斯酸添加物形成的实验研究.
- 研究FLP与基和基脱反应的反应.
主要成果:
- 环烯酸形成易斯酸添加物与三 (PPh3).
- 固态要求高的氨酸会导致丧的易斯对 (FLP) 的形成.
- 通过添加或去质子化,FLPs与基因发生反应,形成新的C-C键.
结论:
- 缺电子的环烯酸是有效的易斯酸.
- 丧的易斯对化学可以扩展到非局部化的π-.
- 这项工作提供了使用环烯酸和FLP形成C-C键的新合成途径.
相关概念视频
Aromatic Hydrocarbon Cations: Structural Overview
2.8K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
Removing one hydrogen from the intervening CH2 group...
2.8K
Lewis Acids and Bases
14.1K
This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
14.1K
Aromatic Hydrocarbon Anions: Structural Overview
2.8K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
Due to the absence of continuous...
2.8K
Electrophiles
10.8K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
10.8K
Electrophilic Addition to Alkynes: Halogenation
8.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation
3.6K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.6K


