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Updated: Apr 23, 2026

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

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N-トリフリルフォスフォラミドのメカニズムと選択性は,ヒドラゾンとアルケンの間のサイクロアディションを (3(+) +2) 触媒化しています

Xin Hong1, Hatice Başpınar Küçük, Modhu Sudan Maji

  • 1Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.

Journal of the American Chemical Society
|September 17, 2014
PubMed
まとめ

高酸性キラルN-トリフリルフォスフォラミドは,ヒドラゾンとアルケンのエナチオセレクティブサイクロアディションを効率的に触媒化し,ピラゾリジンを形成します. この研究は,そのメカニズムを明らかにし,反応効率と選択性における酸強さの重要な役割を強調しています.

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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.
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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