A facile access to chalcogen and dichalcogen bearing dialkylamines and diols

Milton, Marilyn Daisy; Khan, Shabana; Singh, Jai; Mishra, Vivek; Khandelwal, B. L.

doi:10.1016/j.tetlet.2004.12.035

Cited by 34 publications

(19 citation statements)

References 20 publications

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“…All reactions were monitored by thin layer chromatography (TLC) by visualizing with ultraviolet light (UV), and column chromatography purifications were carried out with silica gel. Bis(2‐aminoethyl) ether,16 bis(2‐aminoethyl) thioether,17 and bis(2‐aminoethyl) selenoether18 were synthesized according to previously reported methods with minor modifications (Scheme ). Briefly, bis(2‐aminoethyl) ether 2 could be prepared from 2‐(2‐hydroxyethoxy)ethanol by sulfonation followed by azidation and azide reduction.…”

Section: Methodsmentioning

confidence: 99%

Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens

et al. 2015

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A new family of bipodal anion transporters based on chalcogen‐containing scaffolds has been designed and synthesized. Though structurally related to the well‐studied tripodal anionophores, these molecules are simpler with only two anion‐binding sites. However, the activities remain high. Anion transport could be facilitated by the new transporter at an exceptionally low loading of transporter/lipid ratio of 1:500000. This impressive efficiency is comparable with the most active one from the tren‐based tripodal series. To investigate influences from different scaffolds and substituent groups, lipophilicity, anion‐binding property, and transport activity of each molecule were studied. It was found that the bridge atom has a major impact on transport activities mainly as a result of anion‐binding differences. The results also suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities.

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Section: Methodsmentioning

confidence: 99%

Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens

et al. 2015

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“…Diphenyl diselenide, 17 sodium phenyl selenolate, 18 and disodium diselenide 19 were prepared according to published procedures. 2-Chlorophenyl methanethiol was obtained from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Spectral Characterization, and Crystal Structure of Two Polymorphs of o,o’-Dichloro Dibenzyl Disulfide

Srivastava

Rastogi

Rajaram

et al. 2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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2-Chlorophenyl methanethiol undergoes air oxidation catalyzed by different selenides andyields the corresponding disulfide 1 in two polymorphic forms, 1a and 1b. In the molecular structures of the two new polymorphs of o,o -dichloro dibenzyl disulfide, the dihedral angles between the dibenzyl groups are 82.0(1) • , (1a), and 73.7(4) • , (1b), respectively [(1a): P-1, a = 8.424(2) Å, b = 8.838(2) Å, c = 10.5823(19) Å, α = 90.122(18) • , β = 112.19(2) • , γ = 95.19(2) • , V = 725.9(3) Å 3 ; (1b): P2 1 /n, a = 10.5888(10) Å, b = 9.1590(6) Å, c = 15.2489(14) Å, β = 103.072(9) • , V = 1440.6(2) Å 3 ]. MOPAC computational studies yield dihedral angles of 89.6(5) • and 71.9(9) • . Crystal packing is stabilized by weak π -ring (C H· · ·Cg) intermolecular interactions in both 1a and 1b and by additional weak Cg · · · Cg intermolecular interactions in 1b, which influence the bond distances, bond angles, and torsion angles of the dibenzyl groups in each polymorph. Additional characterization of each polymorph has been carried out by TEM, IR, 1 H and 13 C NMR spectroscopy, microanalysis, and by FAB mass spectrometry. TEM studies of a sample of 1a show that it contains cigar-shaped crystallites.

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“…Only a few examples of β‐amino substituted systems, including tellurocystine and tellurolanthionine derivatives, obtained from suitable β‐haloamines or β‐lactones have been reported. In this context, the nucleophilic ring‐opening‐reaction (NROR) of strained heterocycles such as epoxides, aziridines and thiiranes, as well as the telluro‐Michael addition, could represent powerful as yet unexploited tools to access O‐, N‐, and S‐containing symmetrical dialkyl tellurides and ditellurides.…”

Section: Introductionmentioning

confidence: 99%

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

2020

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The on water reaction of sodium telluride with electrophiles has been explored. Na2Te, generated in situ through the rongalite (sodium hydroxymethanesulfinate)‐promoted reduction of elemental tellurium, reacts with a wide variety of electrophiles, including strained heterocycles, haloalkanes, Michael acceptors, and aryl diazonium salts, providing simple and rapid access to a broad range of novel functionalised symmetrical tellurides. The methodology well tolerated the presence of versatile functional groups such as alchohols, amines, esters, nitriles, and sulfones and allowed the incorporation of tellurium atoms into biologically relevant natural‐derived products. Furthermore, in the case of the nucleophilic ring opening of epoxides and aziridines, a judicious tuning of the reaction conditions enabled the synthesis of unreported β‐hydroxy‐ and β‐amino‐ditellurides, which were further employed as precursors of new functionalised unsymmetrical dialkyl tellurides. The thiol−peroxidase catalytic activity of hydroxy‐ditellurides has also been investigated in order to compare their antioxidant properties with those of homologous tellurides.

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A facile access to chalcogen and dichalcogen bearing dialkylamines and diols

Cited by 34 publications

References 20 publications

Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens

Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens

Synthesis, Spectral Characterization, and Crystal Structure of Two Polymorphs of o,o’-Dichloro Dibenzyl Disulfide

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

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