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Preparation and transformations of acetophenone-derived enamino ketones, BF▫$_2$▫-▫$beta$▫-ketoiminates, and BF▫$_2$▫-▫$beta$▫-diketonates

Year: 2025

Type: article

Abstract: A series of differently substituted β-enaminones 2a,b, 4a–i, 8a–d, and 9–13, their BF$_2$-β-ketoiminate complexes 5a–d, and BF$_2$-β-diketonate complexes 6a–d were prepared as model substrates for photochemical transformations. The attempted photochemical transformations of enaminones 2, 4, 8 and BF$_2$-β-ketoiminate complexes 5 failed. On the other hand, irradiation of mixtures of BF$_2$-β-diketonate complexes 6a–d and cycloalkanes with UV-A light (365 nm) gave the corresponding De Mayo reaction products 7a–f in 9–30% yields. The photochemical ring-expansion of acetyl tetralone-derived BF$_2$-complex 6d gave novel diannulated cyclooctane derivatives 7e and 7f, which would be difficult to obtain using conventional cyclization methods.

Source: Repository of the University of Ljubljana (University of Ljubljana)

Authors: Brodnik, Helena, Ciber, Luka, Grošelj, Uroš, Petek, Nejc, Štefane, Bogdan, Svete, Jurij

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W7024134172

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