Y-aromaticity – existing: yes or no? An answer given on the magnetic criterion (TSNMRS)

Kleinpeter, Erich; Koch, Andreas

doi:10.1016/j.tet.2016.02.020

Cited by 8 publications

(7 citation statements)

References 74 publications

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“…The initial event may be the formation of dianione 5 from amine 1 and CS 2 . Dianione 5 is a heteroanalogue of guanidinium cation with noticeable resonance stabilization energy of Y-shaped species with 4n + 2 π-electrons, which suggest potential Y-aromaticity in these structures [24,25]. Formation of a Y-delocalized intermediate, such as the carbamodithioate dianione 5, may act as a driving force for chemical transformations.…”

Section: Resultsmentioning

confidence: 99%

A one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thiones from primary amines, CS2 and N,N’-diphenyloxalimidoyl dichloride

2016

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activities [1], while others have found application as liquid crystals [6] and cosmetic sunscreens [7].Recently, new methods for the synthesis of 1,3-thiazole derivatives have been reported [8][9][10][11][12]. 1,3-Thiazolidine-2-thione derivatives contain a carbamodithioate moiety and have received considerable attention due to their numerous biological activities and their pivotal role in agriculture and as linkers in solid-phase organic synthesis [13][14][15]. The reaction of dianionic compounds with oxaldiimidoyl dichlorides has been reviewed [16]. Therefore, synthesis of these compounds received considerable attention. Previously, several examples of the reaction between dithiocarbamates with nitrogen-containing derivates of oxalic acid have been reported [17].As part of our current studies on the synthesis of sulfurcontaining organic compounds [18][19][20][21], we describe an efficient one-pot method for the direct synthesis of functionalized cyclic carbamodithioate from the reaction of primary amines (1) and CS 2 in the presence of N,N'-diphenyloxalimidoyl dichloride (3) at room temperature. ExperimentalPrimary amine, CS 2 , solvents were obtained from Merck and used without further purification. N,N'-diphenyloxalimidoyl dichloride (3) was synthesized according to the reported procedure. M.p.: Electrothermal-9100 apparatus. IR spectra: Shimadzu IR-460 spectrometer; band positions in cm −1 . 1 H and 13 C NMR spectra: Bruker DRX-300 Avance instrument at 300 and 75 MHz, respectively; δ in ppm, J in Hz. MS: Finnigan-MAT-8430EI-MS mass spectrometer; at 70 eV; in m/z (rel. %). Elemental analyses: Vario EL III CHNOS elemental analyzer.Abstract A simple one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thione derivatives through the reaction of primary amines and carbon disulfide in the presence of N,N'-diphenyloxalimidoyl dichloride at room temperature is described. Graphical AbstractCS 2 + NPh PhN Cl Cl + Et 3 N (2 eq) DMF, r.t.; 8 h RN S PhN NPh S R-NH 2

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Section: Resultsmentioning

confidence: 99%

A one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thiones from primary amines, CS2 and N,N’-diphenyloxalimidoyl dichloride

2016

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“…[34] Recently, a complex of Au nanoparticles with magnetic nanoparticles has been synthesized which has shown very successful results in some organic reactions. [35] This complex in the oxidation of tertiary amines showed excellent results with high efficiency. With a magnetic particle, this catalyst is easily removed from the reaction medium using an external magnet and can be retrieved up to 10 times without a significant reduction in catalyst activity (Scheme 1).…”

Section: Modified Magnetic Nanoparticles As Catalyst 21 | Gold Comple...mentioning

confidence: 95%

“…S C H E M E 1 Synthesis of magnetic nanoparticle-supported gold (III)-bipy complex [35] S C H E M E 2 Synthesis of magnetic NPs-supported caffeine-based gold (III) complex [15] Also recently, a new nanocatalyst, Fe 3 O 4 @MCM-41-SB-Pd, was prepared by Ahmadi et al and used in the synthesis of different biaryl compounds via the Suzuki-Miyaura cross-coupling reaction. This catalyst was easily recovered by an external magnetic field and reused several times without a more significant decrease in its catalytic activity (Scheme 4).…”

Section: Palladium Supported On Magnetic Nanoparticlesmentioning

confidence: 99%

Recent developments of metallic nanoparticles and their catalytic activity in organic reactions

Amirmahani

Mahmoodi

Bahramnejad

et al. 2020

J Chinese Chemical Soc

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During the last two decades, with the development of nanotechnology, various nanomaterials have been designed and generated. Among them, hybrid organic–inorganic nanoparticles as a particular immobilizing carrier of the catalyst active sites have shown an important contribution in the current research studies. This is due to the large area and loads of active sites. This prominent review is focused on the novel various exa about the immobilization of nanoparticles with organic compounds as versatile and efficient catalysts in organic syntheses.

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“…The concept of Y-aromaticity was introduced to explain the strong basicity of guanidine [1]. This new concept of aromaticity, which does not premise on the existence of a cyclic πelectron conjugated system to be essential for the conventional aromaticity concept, has an attractive potential as a new working hypothesis for molecular design and till now, many studies have been conducted in this field [2][3][4][5][6][7][8]. However, since a rule corresponding to the 4n + 2 rule [9] in the conventional theory of aromaticity was unknown for Y-aromaticity, systematic studies have not been performed theoretically or experimentally.…”

Section: Introductionmentioning

confidence: 99%

The Study of Y-Aromaticity. IV. Tridentenes with Irregular Arm Lengths

Ohmae

2021

Preprint

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To increase the number of synthetic targets having Y-aromaticity, we proposed (<i>n, l, m</i>)-tridentenes, in which the lengths of the three linear conjugated systems, extending from the central atom of the Y-shaped structure of n-tridentene were made irregular. The calculation results obtained using the semiempirical molecular orbital method suggested the existence of a compound that is energetically stabilized and 43 compounds with expectable kinetic stability.

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Y-aromaticity – existing: yes or no? An answer given on the magnetic criterion (TSNMRS)

Cited by 8 publications

References 74 publications

A one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thiones from primary amines, CS2 and N,N’-diphenyloxalimidoyl dichloride

A one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thiones from primary amines, CS2 and N,N’-diphenyloxalimidoyl dichloride

Recent developments of metallic nanoparticles and their catalytic activity in organic reactions

The Study of Y-Aromaticity. IV. Tridentenes with Irregular Arm Lengths

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