Norrish type II reactions of acyl azolium salts

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2021-11-05 DOI:10.1016/j.tet.2021.132497

Andreas Mavroskoufis, Arielle Rieck, Matthew N. Hopkinson

引用次数: 3

Abstract

The photochemical reactivity of acyl azolium salts derived from aliphatic carboxylic acids has been investigated. These species, which serve as models for intermediates generated in N-heterocyclic carbene (NHC) organocatalysis, undergo Norrish type II elimination reactions under irradiation with UVA light in analogy to structurally related aromatic ketones. Moreover, efficient Norrish-Yang cyclization was observed from an adamantyl-substituted derivative. These results further demonstrate the ability of NHCs to influence the absorption properties and photochemical reactivity of carbonyl groups during a catalytic cycle.

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酰基唑盐的Norrish II型反应

研究了由脂肪族羧酸衍生的酰基唑盐的光化学反应性。这些物种作为n -杂环碳(NHC)有机催化生成中间体的模型，在UVA光照射下进行Norrish II型消除反应，类似于结构相关的芳香酮。此外，从金刚烷基取代衍生物中观察到有效的诺里-杨环化。这些结果进一步证明了NHCs在催化循环中影响羰基的吸收特性和光化学反应活性的能力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.