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Norrish Type II Reactions of Acyl Azolium Salts

Norrish Type II Reactions of Acyl Azolium Salts

Norrish Type II Reactions of Acyl Azolium Salts
Image Credit: Elsevier

A. Mavroskoufis, A. Rieck, M. N. Hopkinson* – 2021

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.

Title
40. Norrish Type II Reactions of Acyl Azolium Salts
Author
A. Mavroskoufis, A. Rieck, M. N. Hopkinson*
Publisher
Elsevier
Date
2021
Identifier
DOI: 10.1016/j.tet.2021.132497
Source(s)
Citation
Tetrahedron 2021, DOI: 10.1016/j.tet.2021.132497. (Part of the article collection "System-Oriented Development of Organocatalysis"; Guest Editor: H. Ohmiya)
Type
Text