Synthesis of (1,3-adamantylene)bis-1,3-dicarbonyl compounds

Turmasova, A. A.; Коншин, В. В.; Konshina, Dzh. N.

doi:10.1134/s1070363214070044

Cited by 5 publications

(5 citation statements)

References 11 publications

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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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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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“…Nie and co-workers synthesized photosensitive resins with excellent etching resistance and heat resistance from 1,3-adamantanediol. Additionally, the bis-hydroxy functional groups give 1,3-adamantanediol an advantage in the preparation of polymers. − For example, Fu and co-workers synthesized a polycarbonate using 1,3-adamantanediol and diphenyl phosphoryl chloride, which is an effective halogen-free flame retardant. Zhenhua and co-workers introduced adamantane into the structure of polyimide, which can significantly improve its transparency and heat resistance.…”

Section: Introductionmentioning

confidence: 99%

Practical and Scalable Synthesis of 1,3-Adamantanediol

Hao,

Chen,

Yang

et al. 2024

Org. Process Res. Dev.

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A new method for the efficient synthesis of 1,3-adamantanediol is proposed. It has the advantages of good reaction selectivity, high isolated yield, easy purification, and safe operation. 3-Hydroxyadamantane-1-carboxylic acid reacts first with thionyl chloride to form 1,3-dichloro adamantane, which is then converted to 1,3-adamantanediol in a "triethylamine−water" solution. Three reaction types are involved: chlorination, decarbonylation, and hydrolysis. Under optimal reaction conditions, total isolated yields of up to 95% and purities of up to 99% were achieved. Isolated yields of 100 g per batch have been achieved, with potential for industrial production. We completed the decarbonylation of acyl chloride without the use of a metal catalyst. In addition, the reaction mechanism was investigated by combining experimental data and density functional theory.

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“…[54][55][56][57]. Turmasova et al [54] described the alkylation of dicarbonyl compounds with adamantan-1-ol in 1,2-dichloroethane, catalyzed by indium, gallium, scandium, and copper trifluoromethanesulfonates.…”

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confidence: 99%

“…The best yields of adamantyl derivatives were obtained in the presence of In(OTf) 3 . Depending on the reaction time, selective replacement of one or both hydroxy groups in adamantane-1,3-diol can be achieved [55] (Scheme 47). Apart from adamantan-1-ol, 1-chloroand 1-bromoadamantanes were used to alkylate acetylacetone in the presence of iron and manganese acetylacetonates, and the yields of 2-(adamantan-1-yl)pentane-2,4-dione were 75 and 93%, respectively [56].…”

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confidence: 99%