在环形反应中Thioalkynes
Lifen Peng1, Zhiwen Yuan1, Zilong Tang1
1Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, China.
提奥尔基因是合成多种有机循环的多功能构件,包括三到六个成员和化环. 本综述强调了它们在有机合成中的应用,提供了易于获得有价值的循环化合物的机会.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 有机循环化合物具有独特的特性,对化学,药理学和材料科学至关重要.
- 由于其可访问性,Thioalkynes越来越被认为是有价值的synthons.
研究的目的:
- 审查和突出构建各种有机循环使用 thioalkynes 作为关键构建块的结构.
- 在合成各种有机环系统中对 thioalkynes 的应用进行分类和详细说明.
主要方法:
- 总结了合成策略,以获取三,四,五,六个组成的和合的有机循环从thioalkynes.
- 提供可信的反应机制,用于 thioalkyne-mediated 循环,如果有.
主要成果:
- 提奥尔基因使各种异环和碳环的合成成为可能,包括2H-阿齐林,循环,循环,硫,氧和[b]硫.
- 通过 thioalkyne 化学证明了对广泛的有机循环结构的轻松获取.
结论:
- 提奥尔基因是非常通用的合成子,用于构建广泛的有机循环化合物.
- 本综述巩固了硫基因在有机合成中的合成实用性,强调它们在访问有价值的循环框架中的作用.
相关概念视频
Electrophilic Addition to Alkynes: Halogenation
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.
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.


