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Norrish Type II Reactions of Acyl Azolium Salts

Lookup NU author(s): Dr Matt HopkinsonORCiD

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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.

Publication metadata

Author(s): Mavroskoufis A, Rieck A, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2021

Volume: 100

Print publication date: 05/11/2021

Online publication date: 09/10/2021

Acceptance date: 07/10/2021

Date deposited: 22/11/2021

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Elsevier Ltd

URL: https://doi.org/10.1016/j.tet.2021.132497

DOI: 10.1016/j.tet.2021.132497

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