通过3-甲基-1-烯罗 (I) 进行烯的维尼基cyclopropanation
Tomoya Miura1, Taisuke Sasaki, Tatsuro Harumashi
1Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Japan.
Journal of the American Chemical Society
|February 24, 2006
概括
研究人员开发了新的循环化反应,使用基 ((I) 作为一种等价于形成乙烯基cyclopropanes. vinylcyclopropanes. 的基. 这种方法有效地将乙烯基cyclopropanes 安装到复杂的循环结构通过多个碳-碳键形成在一个步骤.
科学领域:
- 有机化学 有机化学
- 有机金属化学 有机金属化学
- 合成化学 合成化学
背景情况:
- 乙烯基cyclopropanes是有机合成中有价值的结构图案.
- 构建乙烯基cyclopropanes的高效方法,特别是在复杂的分子内,是非常受欢迎的.
研究的目的:
- 开发用于合成乙烯基cyclopropanes的新循环化反应.
- 在有机合成中利用基 ((I) 复合物作为新型碳等价物.
主要方法:
- 循环反应的发展涉及基 (I) 种.
- 作为一个离开的组,在等离子位置使用甲基组.
- 使用基 (基) 作为一个基碳等价物.
主要成果:
- 通过新的循环化途径成功形成乙烯基cyclopropanes.
- 在复杂的循环结构中安装乙烯基cyclopropane单元的演示.
- 在单个合成操作中实现了多个碳-碳键形成.
结论:
- 开发的协议提供了一条有效的通道到乙烯基cyclopropanes.
- 基 ((I) 复合物作为有效的基碳等价物.
- 这种方法允许快速构建含有乙烯基cyclopropane部分的复杂循环结构.
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Preparation of Alkynes: Alkylation Reaction
Introduction
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.
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.
Nitriles to Carboxylic Acids: Hydrolysis
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
Nitriles to Ketones: Grignard Reaction
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard reagent...
The mechanism begins with a nucleophilic attack by the Grignard reagent...
Electrophilic Aromatic Substitution: Nitration of Benzene
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.
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Nitrosation of Enols
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.


