Adamantylation of β-dicarbonyl compounds

The catalyst H3+xPMo12−x+6Mox+5O40 supported on SiO2 was developed for peroxidation of 1,3‐ and 1,5‐diketones with hydrogen peroxide with the formation of bridged 1,2,4,5‐tetraoxanes and bridged 1,2,4‐trioxolanes (ozonides) with high yield based on isolated products (up to 86 and 90 %, respectively) under heterogeneous conditions. Synthesis of peroxides under heterogeneous conditions is a rare process and represents a challenge for this field of chemistry, because peroxides tend to decompose on the surface of a catalyst . A new class of antifungal agents for crop protection, that is, cyclic peroxides: bridged 1,2,4,5‐tetraoxanes and bridged ozonides, was discovered. Some ozonides and tetraoxanes exhibit a very high antifungal activity and are superior to commercial fungicides, such as Triadimefon and Kresoxim‐methyl. It is important to note that none of the fungicides used in agricultural chemistry contains a peroxide fragment.

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“…The other 1,5‐diketones are known compounds. 1,3‐Diketones 4 a – 4 h , 4 k , 4 i , and 4 j , were synthesized according to the known procedures.…”

Section: Methodsmentioning

confidence: 99%

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

Yaremenko

Radulov

Belyakova

et al. 2020

Chemistry A European J

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“…The structure of compound I was proved by IR and 1 H and 13 C NMR spectroscopy, mass spectrometry, and comparison with published data [3,7]. The IR spectrum of I contained absorption bands in the region 1750-1780 cm -1 due to stretching vibrations of the carbonyl groups (diketone tautomer).…”

Section: Iia-iicmentioning

confidence: 80%

Synthesis of 3-(adamantan-1-yl)pentane-2,4-dione from 1-bromo(chloro, hydroxy)adamantane and acetylacetone in the presence of metal complex catalysts

2014

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“…Earlier, our research team hadshown Lewis acids from a series of metal triflates to be efficient catalysts for adamantylation of C-nucleophiles, such as 1,3-dicarbonylcompounds [12,13]. In this work, we decided to use a catalyst from the same series, namely aluminum triflate which has been used earlier to alkylate different N-nucleophiles with propargyl alcohols [14].…”

Section: Resultsmentioning

confidence: 99%

Aluminum Triflate—Catalyzed Adamantylation of N-Nucleophiles

Коншин¹,

Shcherbinin²,

Lupanova³

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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An efficient method is proposed for N-adamantylation of primary carboxamides and sulfonamides, ethyl carbamate, and 4-nitroaniline using the stoichiometric amount of 1-adamantanol in the presence of 5 mol% aluminum triflate in nitromethane. Similarities and differences between adamantylation of some azoles catalyzed by aluminum triflate in nitromethane and the reaction catalyzed by Brønsted acids were revealed.

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Adamantylation of β-dicarbonyl compounds

Cited by 8 publications

References 23 publications

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

Synthesis of 3-(adamantan-1-yl)pentane-2,4-dione from 1-bromo(chloro, hydroxy)adamantane and acetylacetone in the presence of metal complex catalysts

Aluminum Triflate—Catalyzed Adamantylation of N-Nucleophiles

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