- The S2 oxygen atoms are essential for the pronounced fungitoxicity of the sulfur-rich natural product, dysoxysulfone
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Synthesis and antifungal testing of 2,4,5,7,9-pentathiadecane 9,9-dioxide has established that the absence of oxygen atoms on S2 significantly attenuates fungitoxicity in accord with our earlier proposal. Attempts to convert that compound into dysoxysulfone led to the discovery of a novel oxidative conversion of unsymmetrical γ-sulfonyl disulfides into the corresponding symmetrical γ-sulfonyl disulfides. CSIRO 2005.
- Bewick, Sharon A.,Duffy, Stephen,Fletcher, Stephen P.,Langler, Richard F.,Morrison, Heather G.,O'Brien, Erin M.,Ross, Charles,Stephenson, Vanessa C.
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Read Online
- NFSI-catalyzed S[sbnd]S bond exchange reaction for the synthesis of unsymmetrical disulfides
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The metal-free S[sbnd]S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.
- Hu, Qingyue,Li, Zheng-Yi,Song, Mengjie,Sun, Xiaoqiang,Yang, Ke
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supporting information
(2022/01/26)
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- PdCl2/DMSO-Catalyzed Thiol-Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
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Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals. Disulfide-containing organic dyes have also been prepared. This transformation could be extended to thiol-diselenide or thiol-ditelluride exchange affording RS-SeR′ or RS-TeR′.
- Guo, Jimin,Zha, Jianjian,Zhang, Tao,Ding, Chang-Hua,Tan, Qitao,Xu, Bin
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supporting information
p. 3167 - 3172
(2021/05/05)
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- Convenient Unsymmetrical Disulfane Synthesis: Basic Zeolite-Catalyzed Thiol-Disulfane Exchange Reaction
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Convenient catalytic synthetic methods for the preparation of unsymmetrical disulfanes are described. Na-exchanged X type zeolite (Na-X), commercially available as MS-13X, effectively catalyzes thiol-disulfane exchange reactions with 1.0 equivalent of thi
- Yamamoto, Eiji,Kawai, Yasutaka,Takakura, Kei,Kimura, Moemi,Murayama, Haruno,Matsueda, Hironobu,Otsuki, Shujiro,Sakata, Hiroshi,Tokunaga, Makoto
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p. 4694 - 4699
(2021/10/14)
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- An Esterase-Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species
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A strategy to deliver a well-defined persulfide species in a biological medium is described. Under near physiological conditions, the persulfide prodrug can be activated by an esterase to generate a “hydroxymethyl persulfide” intermediate, which rapidly collapses to form a defined persulfide. Such persulfide prodrugs can be used either as chemical tools to study persulfide chemistry and biology or for future development as H2S-based therapeutic reagents. Using the persulfide prodrugs developed in this study, the reactivity between S-methyl methanethiosulfonate (MMTS) with persulfide was unambiguously demonstrated. Furthermore, a representative prodrug exhibited potent cardioprotective effects in a murine model of myocardial ischemia-reperfusion (MI/R) injury with a bell shape therapeutic profile.
- Zheng, Yueqin,Yu, Bingchen,Li, Zhen,Yuan, Zhengnan,Organ, Chelsea L.,Trivedi, Rishi K.,Wang, Siming,Lefer, David J.,Wang, Binghe
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supporting information
p. 11749 - 11753
(2017/09/20)
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- Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric the sulfur compounds and its synthetic method
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The invention discloses a synthesis method of aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides as shown in a formula (II) or a formula (IV). According to the synthesis method, with sulfinic acid sodium salt, and halogenated hydrocarbon and Na2S2O3 as reaction materials or Bunte salt as a reaction material instead of the halogenated hydrocarbon and Na2S2O3, the aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides are obtained by reaction in the absence of transition metal. The synthesis method has the advantages that the reaction is efficient; the yield is high; a vulcanizing reagent is cheap, easily available, stable, and free of pungent smell; no strong acid or alkali or extra oxidizing or reducing agent is added in reaction; the condition is relatively mild; and no transition metal is used as a catalyst in the reaction, and therefore the method is economical, practical and friendly to the environment; a reaction substrate is easy to prepare; the reaction efficiency is high after the reaction is amplified, and therefore, the synthesis method has a wide application prospect and practical value.
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Paragraph 0188-0191
(2016/11/17)
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- Transition-metal-free persulfuration to construct unsymmetrical disulfides and mechanistic study of the sulfur redox process
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A sulfur redox process has been developed between sulfinate and thiosulfate, which efficiently affords diverse unsymmetrical disulfides and provides a new method to modify pharmaceuticals and natural products without requiring an extra oxidant or reductant. Gram-scale investigation further demonstrates the practicality and application potential of this process. Isolated key intermediates and a series of control experiments afford an unusual process, which reveals the mechanism of comproportionation and the transition-metal-free sulfur redox process.
- Xiao, Xiao,Feng, Minghao,Jiang, Xuefeng
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p. 4208 - 4211
(2015/03/30)
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- Phosphine-catalyzed disulfide metathesis
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The reaction between disulfides and phosphines generates a reversible disulfide metathesis process. The Royal Society of Chemistry 2008.
- Caraballo, Remi,Rahm, Martin,Vongvilai, Pornrapee,Brinck, Tore,Ramstroem, Olof
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scheme or table
p. 6603 - 6605
(2009/04/20)
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- Cleavage of S-S bond by nitric oxide (NO) in the presence of oxygen: A disproportionation reaction of two disulfides
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Disulfide bond was cleaved by a catalytic amount of nitric oxide in the presence of oxygen, which was confirmed by experiments employing two symmetrical disulfides. The reaction resulted in the formation of unsymmetrical disulfides in nearly 50% yields. The steric hindrance of alkyl disulfide slowed the reaction rate, and an electron-donating group on the aryl disulfide promoted the reaction. The substituent and S-nitrosothiol effects suggested that the reaction was initialized with an oxidative process by NO+.
- Tsutsumi,Itoh,Ohsawa
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p. 1524 - 1528
(2007/10/03)
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- Disproportionation reaction of disulfides promoted by nitric oxide (NO) in the presence of oxygen
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Two disulfides brought about disproportionation reaction to afford an unsymmetrical disulfide in 50% yield with a catalytic amount of nitric oxide in the presence of oxygen. The reaction proceeded faster when alkyl disulfides were employed for the reaction, and the substituent effects suggested that the reaction commenced with an oxidative process.
- Itoh, Takashi,Tsutsumi, Nozomi,Ohsawa, Akio
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p. 2161 - 2166
(2007/10/03)
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- A new electrochemical method of preparation of unsymmetrical disulfides
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A new method is described for the preparation of unsymmetrical disulfides by reaction of the electrogenerated sulfenium cation R1-S+ with thiols or disulfides.
- Do, Quang Tho,Elothmani, Driss,Le Guillanton, Georges,Simonet, Jacques
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p. 3383 - 3384
(2007/10/03)
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- Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines). Synthesis of β-oxoketene dithioacetals, 1,4-dicarbonyl compounds, and allyl sulfoxides
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Reaction of trithiocarbonates with meta-chloroperoxybenzoic acid in CH2Cl2 at 0°C affords the corresponding S-oxides. These sulfines are relatively stable comppounds which can be purified by chromatography. They react readily with organolithiums in THF at -78°C in a thiophilic manner to give carbanions which are stabilized by three sulfur groups. Hydrolysis affords trithioorthoester oxides. The thermal behaviour of these hindered products has been investigated and new rearrangenrent processes have been evidenced. The former carbanions are soft nucleophiles: 1,4-addition of these intermediates to α-enones was achieved selectively to lead to β-oxo ketenedithioacetals, which are easily transformed into 4-oxoalkanethioates. This 'Umpolung' route allows the formal use of the (alkylthio)carbonyl anion. A thiophilic addition was also observed with allylsilanes in the presence of n-Bu4NF furnishing allyl sulfoxides.
- Leriverend, Catherine,Metzner, Patrick,Capperucci, Antonella,Degl'Innocenti, Alessandro
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p. 1323 - 1342
(2007/10/03)
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- Electroreduction of Organic Compounds, 9. - Convenient Electrochemical Preparation of Thioacetals from Dithioesters
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Thioacetals are obtained as main products on electroreduction of alkyl dithiocarboxylates of various types in the presence of dimethyl sulfate in methanol. (Z)- and (E)-1,2-diaryl-1,2-bis(methylthio)ethenes are formed as byproducts.No reduction to form be
- Drosten, Gisela,Mischke, Peter,Voss, Juergen
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p. 1757 - 1762
(2007/10/02)
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- The Reaction of Ph3P+SR with Thiols: A Simple, Efficient Synthesis of Unsymmetrical Disulphides
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Reaction of Ph3P+SRClO4-, prepared electrochemically from RSSR and Ph3P, with thiols in n-hexane at room temperature gave unsymmetrical disulphides in excellent yields with recovery of Ph3P.
- Masui, Masaichiro,Mizuki, Yasuyuki,Sakai, Kiyoshi,Ueda, Chihiro,Ohmori, Hidenobu
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p. 843 - 844
(2007/10/02)
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