一种类型的异环
Marisol Alvarado1, Lauren Tran1, Christina Tönshoff2
1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
Journal of the American Chemical Society
|June 2, 2025
概括
研究人员报告了第一个类型N-hetaryne的合成,一个1,6-BN-aryne,使新的反应和获取新的1,2-azaborine结构.
科学领域:
- 有机化学
- 异环化学
- 合成方法
背景情况:
- N-氨酸是合成异环化合物至关重要的反应性中间体.
- 之前的合成N-hetarynes是有限的,阻碍了对多样化的结构的访问.
研究的目的:
- 实现类型N-hetaryne的第一个溶液相合成.
- 探索这种新型中间体的反应性和合成效用.
主要方法:
- 1,2-阿扎波林衍生的1,6-BN-aryne的溶液相合成
- 在矩阵隔离条件下对1,6-BN-aryne的表征.
- 密度函数理论 (DFT) 计算以阐明电子结构.
主要成果:
- 1,6-BN-aryne (2) 已成功合成并进行了表征.
- 它在 [4+2], [3+2] 和 [2+2] 循环添加和电友芳香替代 (EAS) 中表现出反应性.
- 区域选择性和二元选择性与极化/物种一致.
结论:
- 1,6-BN-aryne存在于 ketenimine 和形式之间的共振中.
- 这种多功能构建块提供了以前无法获得的功能化1,2-azaborines.
相关概念视频
Nomenclature of Aryl and Heterocyclic Amines
2.3K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.3K
Preparation of Nitriles
2.0K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
3.3K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.3K
Five-Membered Heterocyclic Aromatic Compounds: Overview
3.8K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
3.8K
Electrophilic Aromatic Substitution: Nitration of Benzene
5.7K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
5.7K
Basicity of Heterocyclic Aromatic Amines
5.7K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
5.7K


