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Автор: Grafiati

Опубліковано: 18 травня 2024

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1

Furukawa, Naomichi, Hisashi Fujihara, and Akira Kawada. "Formation of Dithioether Diactions of Cyclic Dithioethers in Concentrated Sulfuric Acid." HETEROCYCLES 24, no. 1 (1986): 17. http://dx.doi.org/10.3987/r-1986-01-0017.

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2

Kundu, Samir, Babli Roy, and Basudeb Basu. "Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers." Beilstein Journal of Organic Chemistry 10 (January 7, 2014): 26–33. http://dx.doi.org/10.3762/bjoc.10.5.

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The development of a silica-promoted highly selective synthesis of 1,2 or 1,3-dithioethers via solvent-free one-pot tandem reactions of an allyl bromide with excess thiol at room temperature is described. The choice of silica gel, either pre-calcined or moistened with water, exhibited notable regioselectivity in the formation of dithioethers. Plausible mechanistic routes were explored and postulated.

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3

Moorhoff, Cornelis M., Wayne D. Cook, Fei Chen, Dat Nghiem, Carl Braybrook, San H. Thang, Jiazeng Sun, Timothy F. Scott, and Christopher N. Bowman. "Synthesis of Acyclic, Symmetrical 3,3'-Allyl Dithioethers, from the Alkylation of 3-Mercapto-2-mercaptomethylprop-1-ene in the Presence of Sodium Hydride." Australian Journal of Chemistry 64, no. 8 (2011): 1083. http://dx.doi.org/10.1071/ch11117.

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A novel method where 3,3′-allyl dithioethers have been prepared from 3-mercapto-2-mercaptomethylprop-1-ene and two mol equivalent of alkyl halide in the presence of two mol equivalent of sodium hydride has been developed. Using this method, bisepoxide, 2,2′-(2-methylenepropane-1,3-diyl)bis(sulfanediyl)bis(methylene)dioxirane (8) has been synthesized from epichlorohydrin, whereas potassium carbonate was unable to deliver this product. These 3,3′-allyl dithioethers can be utilized either as monomers, or with further chemical reactions transformed into more complex monomers, for photoplastic polymer networks.

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4

Yuan, Xiao, Xiaoju Tan, Na Ding, Yongchun Liu, Xiaoxiao Li, and Zhigang Zhao. "NIS-promoted intermolecular bis-sulfenylation of allenamides via a two-step radical process: synthesis of 1,3-dithioethers." Organic Chemistry Frontiers 7, no. 18 (2020): 2725–30. http://dx.doi.org/10.1039/d0qo00690d.

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5

Yu, Guodian, Yingcong Ou, Danyao Chen, Yuanting Huang, Yan Yan, and Qian Chen. "Air-Induced Disulfenylation of Alkenes: Facile Synthesis of Vicinal Dithioethers." Synlett 31, no. 01 (November 19, 2019): 83–86. http://dx.doi.org/10.1055/s-0039-1691493.

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A novel disulfenylation of alkenes with thiophenols and their corresponding disulfides by using air as the oxidant has been achieved. This transformation provides a facile and practical protocol for the synthesis of vicinal dithioethers under mild conditions.

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6

Chernova, Nina P., Nurgul A. Pirmanova, Tolebi Dzhienalyev, and Andrei S. Potapov. "Simple Synthesis of Pyrazole-derived Dithioethers." Procedia Chemistry 15 (2015): 277–81. http://dx.doi.org/10.1016/j.proche.2015.10.044.

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7

Heinz, Benjamin, Moritz Balkenhohl, and Paul Knochel. "Thiolation of Pyridine-2-sulfonamides using Magnesium Thiolates." Synthesis 51, no. 23 (September 3, 2019): 4452–62. http://dx.doi.org/10.1055/s-0039-1690199.

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The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functionalized pyridine-2-sulfonamides, which were subsequently converted into the corresponding thioethers. Finally, symmetric or asymmetric diorganodisulfides were employed as electrophiles in a one-pot ortho-functionalization–thiolation procedure, leading to pyridine 2,3-disubstituted dithioethers.

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8

Flores-Santos, Leticia, Erika Martin, Montserrat Diéguez, Anna M. Masdeu-Bultó, and Carmen Claver. "Novel chiral dithioethers derived from l-tartaric acid." Tetrahedron: Asymmetry 12, no. 21 (November 2001): 3029–34. http://dx.doi.org/10.1016/s0957-4166(01)00504-3.

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9

Serita, Masanori, Makiko Tamaoki, and Koichi Itoh. "Vibrational spectra of cyclic dithioethers and their dications. 1. Vibrational spectra and structures of 1,5-dithiacyclooctane and related cyclic dithioethers." Journal of Physical Chemistry 92, no. 7 (April 1988): 1747–51. http://dx.doi.org/10.1021/j100318a010.

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10

Moorhoff, Cornelis M., Wayne D. Cook, Tara Schiller, Carl Braybrook та San H. Thang. "Synthesis of Symmetrical, Substituted (alkane-α,ω-diyl)(bis[3,3′-allyl dithioethers]) Monomers for Photoplastic Polymer Networks". Australian Journal of Chemistry 65, № 8 (2012): 1165. http://dx.doi.org/10.1071/ch12278.

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Анотація:

Novel symmetrical (alkane-α,ω-diyl)(bis[3,3′-allyl dithioethers]) compounds and their ether analogues, have been synthesised from (alkane-α,ω-diyl)bis([2-{chloromethyl}allyl]sulfane) precursors, for use in crosslinked polymers which exhibit photoplastic behaviour. Facile synthesis and purification of these monomers was achieved if the alkane-α,ω-diyl moiety had at least one oxygen atom in this linker. The number of sulfur atoms in these monomers was varied from four to two to zero to produce monomers which can be used to evaluate their importance on the photoplasticity behaviour.

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11

Holmgren, Steven K., Paul B. Savage, John M. Desper, Kurt D. Schladetzky, Douglas R. Powell, and Samuel H. Gellman. "Steric control of oxidation selectivity in macrocyclic phosphine oxide-dithioethers." Tetrahedron 53, no. 36 (August 1997): 12249–62. http://dx.doi.org/10.1016/s0040-4020(97)00557-7.

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12

Balsells, Jaume, Albert Moyano, Miquel A. Pericàs, and Antoni Riera. "Efficient synthesis of chiral acetylene dithioethers in enantiomerically pure form." Tetrahedron: Asymmetry 8, no. 10 (May 1997): 1575–80. http://dx.doi.org/10.1016/s0957-4166(97)00126-2.

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13

Poulain, Sophie, Sandy Julien, and Elisabet Duñach. "Conversion of norbornene derivatives into vicinal-dithioethers via S8 activation." Tetrahedron Letters 46, no. 41 (October 2005): 7077–79. http://dx.doi.org/10.1016/j.tetlet.2005.07.161.

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14

Tamaoki, Makiko, Masanori Serita, Yasushi Shiratori, and Koichi Itoh. "Vibrational spectra of cyclic dithioethers and their dications. 2. Raman spectra and conformations of the monocation radicals and dications of 1,5-dithiacyclooctane and related dithioethers." Journal of Physical Chemistry 93, no. 16 (August 1989): 6052–58. http://dx.doi.org/10.1021/j100353a023.

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15

Cheu, Elizabeth L. S., Donald T. T. Yapp, Brian O. Patrick, and Brian R. James. "Synthesis and characterization of dithioethers, and their RuII and RuIII complexes." Inorganica Chimica Acta 494 (August 2019): 49–54. http://dx.doi.org/10.1016/j.ica.2019.04.056.

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16

Orejón, A., A. M. Masdeu-Bultó, R. Echarri, M. Diéguez, J. Forniés-Cámer, C. Claver, and C. J. Cardin. "Rhodium cationic complexes using dithioethers as chiral ligands. Application in styrene hydroformylation." Journal of Organometallic Chemistry 559, no. 1-2 (May 1998): 23–29. http://dx.doi.org/10.1016/s0022-328x(97)00692-x.

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17

BALSELLS, J., A. MOYANO, M. A. PERICAS, and A. RIERA. "ChemInform Abstract: Efficient Synthesis of Chiral Acetylene Dithioethers in Enantiomerically Pure Form." ChemInform 28, no. 40 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199740110.

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18

HOLMGREN, S. K., P. B. SAVAGE, J. M. DESPER, K. D. SCHLADETZKY, D. R. POWELL, and S. H. GELLMAN. "ChemInform Abstract: Steric Control of Oxidation Selectivity in Macrocyclic Phosphine Oxide-Dithioethers." ChemInform 29, no. 1 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199801198.

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19

Fujihara, Hisashi, Akira Kawada, and Naomichi Furukawa. "Formation and isolation of the dithioether dications of cyclic dithioethers in the reactions of the corresponding S-oxides and S-imine in concentrated sulfuric acid." Journal of Organic Chemistry 52, no. 19 (September 1987): 4254–57. http://dx.doi.org/10.1021/jo00228a018.

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20

Remias, Joseph E., Laurie E. Grove, and Ayusman Sen. "Carbon–sulfur bond cleavage and reduction of thiols and dithioethers under oxidative conditions." Dalton Trans., no. 15 (2003): 3067–70. http://dx.doi.org/10.1039/b303912a.

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21

Abel, Edward W., Ian Moss, Keith G. Orrell, and Vladimir Sĭk. "Steric influences on sulphur inversion barriers in group 6a tetracarbonyl complexes of dithioethers." Journal of Organometallic Chemistry 326, no. 2 (June 1987): 187–200. http://dx.doi.org/10.1016/0022-328x(87)80156-0.

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22

Abel, Edward W., Ruth Corben, Ian Moss, Keith G. Orrell, Nigel R. Richardson, and Vladimir Sǐk. "The synthesis and dynamic behaviour of halogentricarbonylrhenium(I) complexes of some sterically hindered dithioethers." Journal of Organometallic Chemistry 344, no. 3 (April 1988): 343–50. http://dx.doi.org/10.1016/0022-328x(88)80187-6.

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23

Knorr, M., and F. Guyon. "ChemInform Abstract: Dithioethers as Ligands in Coordination and Organometallic Chemistry: From Molecules to Materials." ChemInform 43, no. 46 (October 18, 2012): no. http://dx.doi.org/10.1002/chin.201246230.

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24

Sunder, Alexander, and Rolf Mülhaupt. "Addition-fragmentation free radical polymerization in the presence of olefinic dithioethers as chain transfer agents." Macromolecular Chemistry and Physics 200, no. 1 (January 1, 1999): 58–64. http://dx.doi.org/10.1002/(sici)1521-3935(19990101)200:1<58::aid-macp58>3.0.co;2-c.

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25

Harvey, Pierre D., and Michael Knorr. "Luminescent Coordination Polymers Built Upon Cu4 X4 (X=Br,I) Clusters and Mono- and Dithioethers." Macromolecular Rapid Communications 31, no. 9-10 (May 11, 2010): 808–26. http://dx.doi.org/10.1002/marc.200900893.

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26

Shen, Hong, Lin Cheng, Huaze Dong, Haibin Zhu, Shaohua Gou, and Xuetai Chen. "Mononuclear and one-dimensional manganese(II) complexes constructed by dithioethers: Effect of flexibility and positional isomerism." Solid State Sciences 12, no. 3 (March 2010): 367–72. http://dx.doi.org/10.1016/j.solidstatesciences.2009.11.015.

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27

Ascenso, José R., Maria de Deus Carvalho, Alberto R. Dias, Carlos C. Romão, Maria J. Calhorda, and Luis F. Veiros. "Nuclear magnetic resonance studies of sulfur inversion in bis(cyclopentadienyl)-molybdenum and -tungsten complexes with dithioethers." Journal of Organometallic Chemistry 470, no. 1-2 (May 1994): 147–52. http://dx.doi.org/10.1016/0022-328x(94)80159-2.

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28

Harvey, Pierre D., and Michael Knorr. "ChemInform Abstract: Luminescent Coordination Polymers Built Upon Cu4X4 (X: Br, I) Clusters and Mono- and Dithioethers." ChemInform 41, no. 39 (September 2, 2010): no. http://dx.doi.org/10.1002/chin.201039227.

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29

Reisgys, Martina, Hartmut Spies, Bernd Johannesn, Hans-Jergen Pietzsch, and Peter Leibnitz. "Synthesis and Structural Characterization of Mixed-Ligand Oxorhenium(V) Complexes Containing Bidentate Dithioethers and Monothiolato Ligands." Chemische Berichte 130, no. 9 (September 1997): 1343–47. http://dx.doi.org/10.1002/cber.19971300927.

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30

Kondo, Teruyuki, Shin-ya Uenoyama, Ken-ichi Fujita, and Take-aki Mitsudo. "First Transition-Metal Complex Catalyzed Addition of Organic Disulfides to Alkenes Enables the Rapid Synthesis ofvicinal-Dithioethers." Journal of the American Chemical Society 121, no. 2 (January 1999): 482–83. http://dx.doi.org/10.1021/ja983497+.

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31

Forristal, Ian, Kevin R. Lawson, and Christopher M. Rayner. "Optically active 2,3-epoxy sulfides as precursors to 3-hydroxy-1,2-dithioethers and 3-hydroxy-1-alkenylthioethers." Tetrahedron Letters 40, no. 38 (September 1999): 7015–18. http://dx.doi.org/10.1016/s0040-4039(99)01427-6.

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32

Fernández, Fernando, Montserrat Gómez, Susanna Jansat, Guillermo Muller, Erika Martin, Leticia Flores-Santos, Paula X. García, et al. "Allylic Alkylations Catalyzed by Palladium Systems Containing Modular Chiral Dithioethers. A Structural Study of the Allylic Intermediates." Organometallics 24, no. 16 (August 2005): 3946–56. http://dx.doi.org/10.1021/om050190s.

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33

Shukurov, S. Sh, M. A. Kukaniev, V. M. Bobogaribov, and S. S. Sabirov. "A new variant of the dithiocarbazate method of synthesis of asymmetric dithioethers of 2,5-dimercapto-1,3,4-thiadiazole." Chemistry of Heterocyclic Compounds 29, no. 8 (August 1993): 980. http://dx.doi.org/10.1007/bf00534284.

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34

Traeger, Juliane, Tillmann Klamroth, Alexandra Kelling, Susanne Lubahn, Ernst Cleve, Wulfhard Mickler, Matthias Heydenreich, Holger Müller, and Hans-Jürgen Holdt. "Complexation of Palladium(II) with Unsaturated Dithioethers - A Systematic Development of Highly Selective Ligands for Solvent Extraction." European Journal of Inorganic Chemistry 2012, no. 14 (February 28, 2012): 2341–52. http://dx.doi.org/10.1002/ejic.201101406.

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35

Jin, Zhuang, Bo Xu, and Gerald B. Hammond. "Green Synthesis of Vicinal Dithioethers and Alkenyl Thioethers from the Reaction of Alkynes and Thiols in Water." European Journal of Organic Chemistry 2010, no. 1 (November 17, 2009): 168–73. http://dx.doi.org/10.1002/ejoc.200901101.

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36

Abel, Edward W., David E. Budgen, Ian Moss, Keith G. Orrell, and Vladimir Šik. "A multinuclear (1H, 13C and 95Mo) NMR investigation of sulphur inversion in molybdenum tetracarbonyl complexes of chelating dithioethers." Journal of Organometallic Chemistry 362, no. 1-2 (February 1989): 105–15. http://dx.doi.org/10.1016/0022-328x(89)85284-2.

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37

SHUKUROV, S. SH, M. A. KUKANIEV, V. M. BOBOGARIBOV, and S. S. SABIROV. "ChemInform Abstract: New Variation of Dithiocarbazate Method for the Synthesis of Unsymmetrical Dithioethers of 2,5-Dimercapto-1,3,4-thiadiazole." ChemInform 25, no. 20 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199420169.

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38

Forristal, Ian, Kevin R. Lawson, and Christopher M. Rayner. "ChemInform Abstract: Optically Active 2,3-Epoxy Sulfides as Precursors to 3-Hydroxy-1,2-dithioethers and 3-Hydroxy-1-alkenylthioethers." ChemInform 30, no. 48 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199948106.

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39

Pietzsch, Hans-Jürgen, Martina Reisgys, Hartmut Spies, Bernd Johannse, and Peter Leibnitz. "Technetium and Rhenium Complexes with Thioether Ligands, 5. Synthesis and Structural Characterization of Neutral Oxorhenium(V) Complexes with Tridentate Dithioethers." Chemische Berichte 130, no. 3 (March 1997): 357–62. http://dx.doi.org/10.1002/cber.19971300309.

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40

Kondo, Teruyuki, Shin-ya Uenoyama, Ken-ichi Fujita, and Take-aki Mitsudo. "ChemInform Abstract: First Transition-Metal Complex Catalyzed Addition of Organic Disulfides to Alkenes Enables the Rapid Synthesis of vicinal-Dithioethers." ChemInform 30, no. 23 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199923072.

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41

Basu, Basudeb, Kinkar Biswas, Samir Kundu, and Debasish Sengupta. "In Quest of “Stereoselective Switch” for On-Water Hydrothiolation of Terminal Alkynes Using Different Additives and Green Synthesis of Vicinal Dithioethers." Organic Chemistry International 2014 (February 13, 2014): 1–6. http://dx.doi.org/10.1155/2014/358932.

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Анотація:

On-water hydrothiolation reaction between terminal alkyne and thiol has been probed in the presence of various additives. Aromatic alkynes yield corresponding 1-alkenyl sulfides, whereas aliphatic alkynes undergo double-addition yielding vicinal disulfides in good to excellent yields. Formation of 1-alkenyl sulfides proceeds with a high degree of regioselectivity (via anti-Markovnikov addition), and switching the stereoselectivity between E/Z isomers has been noticeably realized in the presence of different additives/promoters.

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42

Abidi, Nissa, and Jason R. Schmink. "Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation." Journal of Organic Chemistry 80, no. 8 (April 7, 2015): 4123–31. http://dx.doi.org/10.1021/acs.joc.5b00547.

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43

Moorhoff, Cornelis M., Wayne D. Cook, and Carl Braybrook. "Novel synthesis of symmetrical 3,3′-allyl dithioethers as photoplastic monomer precursors by equal molar rate addition of reactants and solvent controlled oligomerization." Monatshefte für Chemie - Chemical Monthly 144, no. 6 (April 3, 2013): 891–902. http://dx.doi.org/10.1007/s00706-013-0942-6.

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44

Abidi, Nissa, and Jason R. Schmink. "ChemInform Abstract: Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C-S Bond Formation." ChemInform 46, no. 34 (August 2015): no. http://dx.doi.org/10.1002/chin.201534121.

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45

Traeger, Juliane, Tillmann Klamroth, Alexandra Kelling, Susanne Lubahn, Ernst Cleve, Wulfhard Mickler, Matthias Heydenreich, Holger Müller, and Hans-Jürgen Holdt. "Complexation of Palladium(II) with Unsaturated Dithioethers - A Systematic Development of Highly Selective Ligands for Solvent Extraction (Eur. J. Inorg. Chem. 14/2012)." European Journal of Inorganic Chemistry 2012, no. 14 (May 2012): n/a. http://dx.doi.org/10.1002/ejic.201290041.

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46

Moorhoff, Cornelis M., Wayne D. Cook, and Carl Braybrook. "ChemInform Abstract: Novel Synthesis of Symmetrical 3,3′-Allyl Dithioethers as Photoplastic Monomer Precursors by Equal Molar Rate Addition of Reactants and Solvent Controlled Oligomerization." ChemInform 44, no. 35 (August 8, 2013): no. http://dx.doi.org/10.1002/chin.201335040.

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47

Traeger, J., A. Kelling, U. Schilde, and H. J. Holdt. "rac-1-[(2-Methoxyethyl)sulfanyl]-2-[(2-methoxyethyl)sulfinyl]benzene and its PdCl2complex." Acta Crystallographica Section C Crystal Structure Communications 68, no. 9 (August 1, 2012): m238—m241. http://dx.doi.org/10.1107/s0108270112032192.

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Анотація:

As an extension of recent findings on the recovery of palladium with dithioether extractants, single crystals of the chelating vicinal thioether sulfoxide ligandrac-1-[(2-methoxyethyl)sulfanyl]-2-[(2-methoxyethyl)sulfinyl]benzene, C12H18O3S2, (I), and its square-planar dichloridopalladium complex,rac-dichlorido{1-[(2-methoxyethyl)sulfanyl]-2-[(2-methoxyethyl)sulfinyl]benzene-κ2S,S′}palladium(II), [PdCl2(C12H18O3S2)], (II), have been synthesized and their structures analysed. The molecular structure of (II) is the first ever characterized involving a dihalogenide–PdIIcomplex in which the palladium is bonded to both a thioether and a sulfoxide functional group. The structural and stereochemical characteristics of the ligand are compared with those of the analogous dithioether compound [Traegeret al.(2012).Eur. J. Inorg. Chem.pp. 2341–2352]. The sulfinyl O atom suppresses the electron-pushing and mesomeric effect of the S—C...;C—S unit in ligand (I), resulting in bond lengths significantly different than in the dithioether reference compound. In contrast, in complex (II), those bond lengths are nearly the same as in the analogous dithioether complex. As observed previously, there is an interaction between the central PdIIatom and the O atom that is situated above the plane.

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48

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50

Mosberg, Henry I., and John R. Omnaas. "Dithioether-containing cyclic peptides." Journal of the American Chemical Society 107, no. 10 (May 1985): 2986–87. http://dx.doi.org/10.1021/ja00296a033.

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