Fused 1,2‐Dithioles. Part VII

Stachel, Hans‐Dietrich; Zimmer, Barbara; Eckl, E.; Semmlinger, Katharina; Weigand, Wolfgang; Wünsch, Ralf; Mayer, Péter

doi:10.1002/hlca.200590101

Cited by 12 publications

(6 citation statements)

References 20 publications

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“…Pharmaceutically active disulfides are known to have anti‐inflammatory, antitumour, antioxidants and antiulcer activities. Chemically, organo‐disulfides are being used in catalyst, in ligand designing, towards producing fine chemicals and in functional group protections . In addition, the concept of constitutional dynamic chemistry (CDC) and dynamic combinatorial chemistry (DCC) is documented using the chemistry of disulfides.…”

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confidence: 99%

“…[5] Pharmaceutically active disulfides are known to have anti-inflammatory, [6] antitumour, [7] antioxidants [8] and antiulcer [9] activities. [12] In addition, the concept of constitutional dynamic chemistry (CDC) [13] and dynamic combinatorial chemistry (DCC) [14] is documented using the chemistry of disulfides. [12] In addition, the concept of constitutional dynamic chemistry (CDC) [13] and dynamic combinatorial chemistry (DCC) [14] is documented using the chemistry of disulfides.…”

mentioning

confidence: 99%

“…Chemically,o rgano-disulfides are being used in catalyst, [10] in ligand designing, [11] towards producing fine chemicals andi n functional group protections. [12] In addition, the concept of constitutional dynamic chemistry (CDC) [13] and dynamic combinatorial chemistry (DCC) [14] is documented using the chemistry of disulfides. Due to the reversibility nature of the disulfide bond, formation of many products could be possible when more than one thiol building blocks present in equilibrium.…”

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Unsymmetrical Disulfides Synthesis via Sulfenium Ion

Parida

Choudhuri

Mal

2019

Chemistry An Asian Journal

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An umpolunga pproachf or the synthesis of unsymmetrical disulfides via sulfenium ion is reported.I ns itu generated electrophilic sulfeniumi on from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalysta nd 4-dimethylaminopyridine (DMAP)/water as promoter,t he target syntheses were achieved in one pot under aerobic condition.Organicd isulfides are important functional moieties found in variousm arine natural products, [1] pharmaceuticals, [2] materials [3] and polymers. [4] Disulfides are also known for their odors especially in kitchen items, like in onions and garlics. [5] Pharmaceutically active disulfides are known to have anti-inflammatory, [6] antitumour, [7] antioxidants [8] and antiulcer [9] activities. Chemically,o rgano-disulfides are being used in catalyst, [10] in ligand designing, [11] towards producing fine chemicals andi n functional group protections. [12] In addition, the concept of constitutional dynamic chemistry (CDC) [13] and dynamic combinatorial chemistry (DCC) [14] is documented using the chemistry of disulfides. Due to the reversibility nature of the disulfide bond, formation of many products could be possible when more than one thiol building blocks present in equilibrium. [15] Therefore, it's always challengingt os ynthesize selectively any unsymmetrical disulfides from mixtureo ft hiols in one pot. [16] In Figure 1a,f ew examples of either pharmaceutically important or naturallyo ccurring molecules containing disulfides functionalities are shown. [16b] The known approaches for the synthesis of disulfides are mainly based on using molecular oxygen, [17] transition metals, [18] phosphine-free cationic rhodium(I) complex catalyst, [19] Cu I -phenanthroline catalyst, [20] base catalyzed, [21] non-transition metals, [22] oxidants, [23] sodium perborate, [24] metal organicf rame works (MOFs), [25] microwavea ssisted, [26] electrochemical methods, [27] etc. Recently Dethe and co-workersd eveloped synthesis of unsymmetrical disulfides using fac-Ir(ppy) 3 as photocatalyst and visible light from white LED (Figure 1b). [28] Similarly,u nsymmetrical disulfide synthesis is also reported using O 2 as the oxidant and cobalt(II)phthalocyanine-tetra-sodium sulfonate as the catalyst (Figure 1b). [29] Herein, we reporto ne pot synthesis of unsymmetrical organodisulfides ( Figure 1c)v ia umpolung approach in ethanol sol-

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Unsymmetrical Disulfides Synthesis via Sulfenium Ion

Parida

Choudhuri

Mal

2019

Chemistry An Asian Journal

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“…The NMR signal of the olefinic H-atom of 10b appeared at d 5.55 [19]. This signal disappeared upon addition of D 2 A C H T U N G T R E N N U N G O.…”

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“…Because of the structural similarity of the alkylidene-sultams 9a,b and the alkylidene-lactam 1a, we were not surprised that selective ozonolysis of 9a,b took place furnishing the sulfonimides 11a,b. The same compounds were obtained by ozonation of the sultams 10a,b [19] (Scheme 2).…”

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Functionalized Imides by Regioselective Ozonation

Poschenrieder¹,

Stachel²,

Eckl³

et al. 2006

Helvetica Chimica Acta

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Ozonations of alkoxy-and (acyloxy)-substituted alkylidene-lactams 1 and 5 or of the alkylidene-sultams 9 and 10 proceeded by regioselective cleavage of the exocyclic C=C bonds (Schemes 1 and 2). These bonds are part of an enamide system and, therefore, possess considerable polarity as shown by 13 C-NMR spectra. As a result, the partly known maleimides 3 and 6 or the sulfonimides 11 were obtained. Compounds 3 and 11 reacted with diazomethane to give the highly reactive bicyclic derivatives 8 and 12, respectively. The cinnamylidene-lactames 16a,b were converted by selective ozonolysis mainly into the formylmethylene lactames 17a,b (Scheme 3). The amino-substituted aldehyde 20 bears a structural relationship to the lactone antibiotic basidalin 21a. The tendency of some donor-substituted maleimides to undergo [2 + 2] cycloadditions was assessed (Scheme 4). The configuration of the photodimers 22a,b and 24a,b was established by X-ray crystallography.Introduction. -The cleavage of alkene C=C bonds by ozone to give aldehydes, ketones, and carboxylic acids was introduced into organic chemistry at the beginning of the 20 th century by Harries [1]. Ozonolyses take place under extremely mild reaction conditions and often with excellent yields. The individual course of an ozonization, however, is strongly dependent on the constitution of the starting material, the solvent, and the choice of reductive or oxidative workup conditions (for a comprehensive review, see [2]).A basic three-step mechanism was formulated by Criegee and is now bearing his name [3]. In a sequence of concerted 1,3-dipolar cycloaddition and cycloreversion, carbonyl oxides [4] are formed which are captured by internally generated carbonyl compounds in another 1,3-dipolar cycloaddition to yield ozonides. As a result, for unsymmetrical alkenes, substituent rules for the regioselective OÀO splitting in the cycloreversion step have been formulated [5] [6]. There are, however, exceptions from these rules, and the ozonide-forming step may be bypassed due to low dipolarophilicity of the carbonyl intermediate. Both is examplified in the ozonolysis of ketene acetals [7]. Modifications of the original Criegee mechanism have been introduced later [8]. An alternative mechanistic concept of ozonations was recently brought up for discussion [9]. According to the donor-acceptor concept, ozonations are regarded as oxidation reactions with radical-ion intermediates.It is well known that the C=C bond of enol ethers is readily cleaved by ozone forming a carbonyl compound and a carboxylic acid ester [10 -14]. Analogously, in the ozonolysis of enol esters, beside a carbonyl compound, a mixed carboxylic acid anhydride is

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Synthesis and Electrochemical Investigations of the [FeFe]‐Hydrogenase H‐Cluster Mimics Mediated by Bicyclic Dithiols Derivative

Daraosheh

Abul‐Futouh

Abdel‐Rahem

et al. 2021

Zeitschrift anorg allge chemie

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Biomimic of the active site of [FeFe]-hydrogenase containing bicyclic dithiols as bridging linker has been synthesized and characterized using different spectroscopic methods. The influence of this linker on the redox properties and the catalytic behavior of the resulted binuclear complex was investigated using cyclic voltammetry, showing that it can catalyze the reduction of protons to H 2 in the presence of acetic acid (AcOH). Moreover, the results revealed that the bicyclic dithiolene linker has improved the chemical stability of the reduced species and caused a shift to less negative potential in comparison to the synthetic models that mimic the active site of [FeFe]-hydrogenase reported in the literature. In addition, the structure of the resulted binuclear complex mediated by bicyclic dithiols as bridging linker was confirmed by X-ray diffraction analysis.

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Fused 1,2‐Dithioles. Part VII

Cited by 12 publications

References 20 publications

Unsymmetrical Disulfides Synthesis via Sulfenium Ion

Unsymmetrical Disulfides Synthesis via Sulfenium Ion

Functionalized Imides by Regioselective Ozonation

Synthesis and Electrochemical Investigations of the [FeFe]‐Hydrogenase H‐Cluster Mimics Mediated by Bicyclic Dithiols Derivative

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