オリゴボランとイソニトリルからBNヘテロサイクルを原子効率的に合成する
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PubMedで要約を見る
まとめ
この要約は機械生成です。O-Xylyl isonitrileは,ボロン-窒素化合物と反応して新しい異環構造を形成する. これらの反応は,複雑なオルガノボロンと窒素を含む分子を合成するための新しい経路を生み出します.
科学分野
- 有機金属化学
- ボロン化学
- ヘテロサイクル化学
背景
- ペラミノトリとテトラボランは基本的なボロン-窒素群である.
- イソニトリルは,無機および有機合成における多用途の反応剤である.
研究 の 目的
- 線形ペラミノトリとテトラボランとのO- キシリルイソニトリルの反応性を調査する.
- 新しいボロン-窒素ヘテロサイクルの形成を調査する.
主な方法
- オキシリルイソニトリルとペラミノトリ=とテトラボランの反応
- 中間製品の熱再配置
- 合成されたヘテロサイクル化合物の特徴
主要な成果
- O-Xylyl isonitrileは,peraminotri-およびテトラボランのB-B結合に挿入されます.
- 2つの異なるCB2Nヘテロサイクルの形成:1-アゾニウム-2,4-ジボレタン-3-イドと1,2,4-アザディボレチジン.
- イソニトリルとのさらなる反応はC2BN2およびC2B2N2ヘテロサイクルを生成する.
結論
- 異なるボロン-窒素ヘテロサイクルの新しい合成経路を示しています.
- 複雑なオルガン・ボロン・フレームワークの構築におけるイソニトリルの有用性を強調する.
- ペラミノボランを含む既知の反応の範囲を拡大する.
関連する概念動画
Introduction
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.
Mechanism
The hydroboration-oxidation reaction is a two-step...
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Borane as a reagent is very reactive, as the...
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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...
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
However, enamines are neutral and less reactive than enolates, which bear a net negative charge. Consequently, enamines are effective Michael donors...
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.
Figure 1: Keto–enol tautomerization
As depicted in Figure 2, when treated with hydrochloric acid, sodium nitrite forms an oxonium ion. The expulsion of a water molecule from the oxonium ion produces a nitrosonium ion.
Figure 2: The chemical reaction of the formation of the...