Synthesis and Keto-Enol Tautomerism of 1-Phenyl(1-thiophen-2-yl)-4-(diphenylphosphoryl)butane-1,3-diones

IF 0.9 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Russian Journal of General Chemistry Pub Date : 2024-08-30 DOI:10.1134/S1070363224070041

D. A. Tatarinov, A. V. Shepelina, E. E. Bajnazarova, M. Ali, A. P. Dovzhenko, R. R. Zairov, V. F. Mironov

引用次数: 0

Abstract

Novel 1-phenyl(1-thiophen-2-yl)-4-(diphenylphosphoryl)butane-1,3-diones were synthesized by the Claisen-type condensation of 1-(diphenylphosphoryl)propan-2-one with ethyl phenyl(thiophene-2-yl)carboxylates. The tautomeric equilibrium of diketone moiety of phosphine oxides was investigated by ¹H and ¹³C{¹H} NMR spectroscopy. Two species out of five possible tautomers (diketo and mono-enol) were observed in the solution of 1-phenyl(1-thiophen-2-yl)-4-(diphenylphosphoryl)butane-1,3-diones. The major tautomer was the mono-enol form with content 80–90%. Furthermore, the double bond position at C³ atom was determined by ¹³C{¹H} NMR spectroscopy.

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1-苯基(1-噻吩-2-基)-4-(二苯基磷酰)丁烷-1,3-二酮的合成与酮烯醇同分异构体

AbstractNovel 1-苯基(1-噻吩-2-基)-4-(二苯基磷酰)丁烷-1,3-二酮是通过 1-(二苯基磷酰)丙-2-酮与苯基(噻吩-2-基)羧酸乙酯的克莱森式缩合合成的。通过 1H 和 13C{1H} NMR 光谱研究了膦氧化物中二酮分子的同分异构平衡。核磁共振光谱进行了研究。在 1-苯基（1-噻吩-2-基）-4-（二苯基磷酰）丁烷-1,3-二酮的溶液中，观察到五种可能的同分异构体中的两种（二酮和单烯醇）。主要的同分异构体是单烯醇形式，含量为 80-90%。此外，13C{1H}核磁共振光谱测定了 C3 原子的双键位置。核磁共振光谱。

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来源期刊

Russian Journal of General Chemistry 化学-化学综合

CiteScore

1.40

自引率

22.20%

发文量

252

审稿时长

2-4 weeks

期刊介绍： Russian Journal of General Chemistry is a journal that covers many problems that are of general interest to the whole community of chemists. The journal is the successor to Russia’s first chemical journal, Zhurnal Russkogo Khimicheskogo Obshchestva (Journal of the Russian Chemical Society ) founded in 1869 to cover all aspects of chemistry. Now the journal is focused on the interdisciplinary areas of chemistry (organometallics, organometalloids, organoinorganic complexes, mechanochemistry, nanochemistry, etc.), new achievements and long-term results in the field. The journal publishes reviews, current scientific papers, letters to the editor, and discussion papers.