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Journal articles on the topic '4-dithiane'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Yates, Peter, Azza Seif-El-Nasr, Jennifer Stanton, and Jiri J. Krepinsky. "Reactions of δ-valerolactone with lithio trithio-orthoformates." Canadian Journal of Chemistry 69, no. 3 (March 1, 1991): 415–22. http://dx.doi.org/10.1139/v91-063.

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δ-Valerolactone (3), on treatment with tris(methylthio)methyllithium (7) followed by weakly acidic aqueous work-up, gave a tautomeric mixture of 1, 1-bis(methylthio)-6-hydroxy-2-hexanone (8a) and tetrahydro-2-bis(methylthio)methyl-2-pyranol (8b). Under analogous conditions 3 reacted with tris(phenylthio)methyllithium (10) to form tetrahydro-3-(phenylthiocarbonyl)-2-pyranone (11). With 2-(methylthio)-1,3-dithian-2-yllithium (16) it gave a tautomeric mixture of 2-(5-hydroxy-1-oxopentyl)-2-(methylthio)-1,3-dithiane (17a) and 2-(tetrahydro-2-hydroxy-2-pyranyl)-2-(methylthio)-1,3-dithiane (17b). Treatment of 17 with methanol in the presence of acidic ion-exchange resin gave a mixture of 2-(5,6-dihydro-3-(methylthio)-2(4H)-pyranyl)-1,3-dithiane (20), 2-(tetrahydro-2-methoxy-2-pyranyl)-1,3-dithiane (21), and 2-(tetrahydro-2-methoxy-4-(methylthio)-2-pyranyl)-1,3-dithiane (22). Similar treatment of 20 gave a mixture of 20, 21, and 22. Compound 21 was synthesized independently by similar treatment of 2-(tetrahydro-2-hydroxy-2-pyranyl)-1,3-dithiane (23). The origins of the anomalous products are discussed briefly. It is concluded that because of these anomalies the preparation of tetrahydro-2-hydroxypyran-2-carboxylic acid acetals and related glycosides via trithio-orthoformate derivatives can encounter difficulties, although dithioacetals may serve this purpose. Key words: 1,3-dithianes, α-hydroxy acids,δ-lactones, trithio-orthoformates.

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2

Li, Zaiguo, Huy Chiu, and Andrei G. Kutateladze. "Photolabile calixarene-based rosette." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 807–10. http://dx.doi.org/10.1139/v03-057.

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A model calix[4]arene-based rosette carrying two alternating photocleavable dithianyl-hydroxy-methyl moieties and two benzophenonecarboxylates was synthesized and shown to be capable of photoinduced fragmentation, with efficiency comparable to that of the externally sensitized parent dithianebenzaldehyde adducts.Key words: photoinduced electron transfer, photofragmentation, calixarene, dithianecarbonyl adducts.

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3

Fun, Hoong-Kun, Reza Kia, Annada C. Maity, and Shyamaprosad Goswami. "2-(4-Nitrophenyl)-1,3-dithiane." Acta Crystallographica Section E Structure Reports Online 65, no. 2 (January 17, 2009): o348. http://dx.doi.org/10.1107/s1600536809001809.

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4

Pinto, B. Mario, Jesus Sandoval-Ramirez, R. Dev Sharma, Anthony C. Willis, and Frederick W. B. Einstein. "Synthesis and conformational analysis of 2-arylseleno-1,3-dithianes. Crystal and molecular structure of 2-(4-methoxyphenylseleno)- and 2-(4-trifluoromethylphenylseleno)-1,3-dithiane." Canadian Journal of Chemistry 64, no. 4 (April 1, 1986): 732–38. http://dx.doi.org/10.1139/v86-118.

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The synthesis of 2-(4-methoxyphenylseleno)-1,3-dithiane 3 and 2-(4-trifluoromethylphenylseleno)-1,3-dithiane 5 from 2-chloro-1,3-dithiane 1 and the corresponding sodium arylselenolates is described. Nuclear magnetic resonance spectroscopic investigation of the products indicates that the compounds exist predominantly in a conformation in which the arylseleno moiety adopts an axial orientation. X-ray crystallographic investigation indicates that the 1,3-dithiane ring exists in the chair conformation with the arylseleno moiety in the axial orientation. Compound 3 is orthorhombic, space group P212121 with a = 5.449(2) Å, b = 9.217(2) Å, c = 24.860(3) Å, V = 1248.5 Å3, Z = 4. The structure was refined to R = 0.038 for 689 reflections with I > 2.3σ(I). Compound 5 is monoclinic, space group C2/c, with a = 28.628(7) Å, b = 5.246(2) Å, c = 21.342(5) Å, β = 121.12(1)°, V = 2743.8 Å3, Z = 8. Its structure refined to R = 0.064 for 966 reflections with I > 2.3σ(I).

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5

Samas, Brian, Cathy Préville, Benjamin A. Thuma, and Vincent Mascitti. "2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-1,3-dithiane." Acta Crystallographica Section E Structure Reports Online 66, no. 6 (May 19, 2010): o1386. http://dx.doi.org/10.1107/s1600536810017393.

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6

Reuter, Hans, Natalia Röwekamp-Krugley, Marius Imwalle, Simona Keil, and Martin Reichelt. "Crystal structure of a one-dimensional coordination polymer of tin(IV) bromide with 1,4-dithiane." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): m267—m268. http://dx.doi.org/10.1107/s2056989015023932.

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The title compound, [SnBr4(C4H8S2)] {systematic name:catena-poly[[tetrabromidotin(IV)]-μ-1,4-dithiane-κ2S:S′]}, represents the first 1,4-dithiane complex with tin as coordination centre. The asymmetric unit consist of half a formula unit with the tin(IV) atom at the centre of symmetry at 0,0,1/2 (Wyckoff symbolb) and a centrosymmetric 1,4-dithiane molecule with the centre of symmetry in 1/2,0,1 (Wyckoff symbolc). The tin(IV) atom is coordinated in a distorted octahedral manner by the four bromine atoms and two sulfur atoms of two 1,4-dithiane molecules in atrans-position. Sn—Br [mean value: 2.561 (5) Å] and Sn—S distances [2.6546 (6) Å] are in the typical range for octahedrally coordinated tin(IV) atoms and the dithiane molecule adopts a chair conformation. The one-dimensional polymeric chains propagate along the [101] direction with weak intermolecular Br...Br [3.5724 (4) Å] between parallel chains and weak Br...H interactions [2.944–2.993 Å] within the chains.

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7

Freudenmann, Dominic, and Claus Feldmann. "[SbCl2(η2-1,4-dt)(μ2-1,4-dt)][AlCl4]: Ionic Liquid-based Synthesis of a Stibenium Cation (dt = dithiane)." Zeitschrift für Naturforschung B 68, no. 10 (October 1, 2013): 1090–94. http://dx.doi.org/10.5560/znb.2013-3133.

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The reaction of antimony(III) chloride with 1,4-dithiane (1,4-dt) in the ionic liquid [BMIM]Cl ([BMIM]Cl: 1-butyl-4-methylimidazolium chloride) with an excess of the Lewis acid AlCl3 results in the formation of a ligand-stabilized stibenium cation [SbCl2]+. 1,4-Dithiane simultaneously serves as a chelating η2-ligand, exhibiting a boat-like conformation, as well as a bridging μ2-ligand, exhibiting a chair-like conformation, with Sb3+ as the coordinating cation. Due to the bridging 1,4-dithiane ligands, a chain-like structural building unit 1∞[SbCl2(η2-1,4-dt)1/1(μ2-1,4-dt)2/2]+ is formed.

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8

Lei, Bo, and Alex G. Fallis. "Cadmium chloride mediated regiocontrol of dienolates and ketene thioacetals: γ condensation with aldehydes." Canadian Journal of Chemistry 69, no. 9 (September 1, 1991): 1450–56. http://dx.doi.org/10.1139/v91-214.

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The use of cadmium chloride to control the regioselectivity of vinylogous anions upon condensation with aldehydes is described. Addition occurred preferentially at the γ position with substituted crotonates and 2-ethylidene-1,3-dithiane (6). Experiments demonstrated that this selectivity arose as a consequence of isomerization of the initially formed kinetic α product to the thermodynamic γ product (e.g., 2 to 4). The optimum results were achieved with 2 equivalents of cadmium chloride and quenching at 0 °C. Key words: vinylogous anions, cadmium, condensation, dithiane.

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9

Cheng, Ping, Wengang Guo, Ping Chen, Yan Liu, Xin Du, and Can Li. "The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst." Chemical Communications 52, no. 16 (2016): 3418–21. http://dx.doi.org/10.1039/c5cc10292h.

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10

Kumar, Sundaravel Vivek, Shanmugam Muthusubramanian, and Subbu Perumal. "A solvent- and catalyst-free domino reaction for the efficient synthesis of 3-arylthiazolidine-2-thiones under microwave irradiation." RSC Advances 5, no. 110 (2015): 90451–56. http://dx.doi.org/10.1039/c5ra19112b.

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A facile synthesis of 4-hydroxy-3-arylthiazolidine-2-thiones through novel domino reactions of aryl isothiocyanates and 1,4-dithiane-2,5-diol under solvent- and catalyst-free microwave irradiation is reported.

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11

Roy, René, and Allan W. Rey. "Controlled diastereoselection in 2-lithio-1,3-dithiane additions onto α-substituted γ-lactols. Model studies toward bryostatins from (R)-pantolactone." Canadian Journal of Chemistry 69, no. 1 (January 1, 1991): 62–69. http://dx.doi.org/10.1139/v91-009.

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Homochiral α-substituted γ-lactols 3 and 4 derived from (R)-pantolactone 1 were used in 2-lithio-1,3-dithiane additions to afford very high controls in diastereoselectivities arising from 1,2-asymmetric inductions. Thus non-chelation controlled nucleophilic addition on 3 gave the anti diastereomer 5 as the major product (92% de), while the chelation controlled addition on 4 furnished the syn diastereomer 7 (96% de) as the almost exclusive product. The stereochemical outcomes of these reactions were proven unambiguously by locking the conformation of the syn- and anti-triol adducts 7 and 8 through their respective acetonides and by nuclear Overhauser enhancement measurements. The lack of 1,3-dioxolane formation in the case of the anti-triol 8 was taken as a further confirmation of the absolute configuration at the newly created stereocenter. Key words: byrostatin, pantolactone, α-hydroxylactol, dithiane.

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12

Zhang, Shaowei, Demin Ren, Xiaolian Hu, Xingliang Fu, and Xiaofang Li. "Synthesis of Spiro Indazole-Tetrahydrothiophenes via Sulfa-Michael/Aldol Cascade Reactions." Journal of Chemical Research 41, no. 11 (November 2017): 641–44. http://dx.doi.org/10.3184/174751917x15094552081170.

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The sulfa-Michael/aldol cascade reaction of 5-arylmethylidene-1-phenyl-6,7-dihydro-1H-indazol-4(5H)-ones and 1,4-dithiane-2,5-diol yielded novel 2′-(4-aryl)-4′-hydroxy-1-phenyl-4′,5′,6,7-tetrahydro-2′H-spiro[indazole-5,3′-thiophen]-4(1H)-ones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS, together with X-ray crystallographic analysis.

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13

Zhu, Yue, Qilin Wang, Haofan Luo, Zijuan Wang, Guolin Zhang, and Yongping Yu. "A Facile and Efﬁcient Approach for the Synthesis of 3-Aryl-4-hydroxy-1,3-thiazolidin-2-ones." Synthesis 51, no. 11 (April 1, 2019): 2397–401. http://dx.doi.org/10.1055/s-0037-1610862.

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A facile and efficient method for the synthesis of 3-aryl-4-hydroxy-1,3-thiazolidin-2-ones by the reaction of 1,4-dithiane-2,5-diol with acyl azides is reported. This reaction proceeded well at 80 °C to afford products in excellent yields for a wide range of substrates. A possible mechanism has been proposed.

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14

Fiedorow, Piotr, Małgorzata Ratajczak-Sitarz, Maria D. Rozwadowska, and Zbigniew Rozwadowski. "Synthesis of (−)-5-amino-2(3,4-dimethoxyphenyl)-4-phenyl-1,3-dithiane." Journal of Molecular Structure 442, no. 1-3 (February 1998): 65–70. http://dx.doi.org/10.1016/s0022-2860(97)00269-x.

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15

Sugawara, Akira, Ryuichi Sugawara, Hirokazu Ito, Hiroshi Tanaka, Toru Segawa, and Ryu Sato. "A Convenient Synthesis of 1,3-Dithiane Derivatives by Reaction of 4-Methyl-1,3-dithiane-2-thione with Grignard Reagents and Butyllithium." Chemistry Letters 20, no. 8 (August 1991): 1315–18. http://dx.doi.org/10.1246/cl.1991.1315.

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16

Yan, Jinlong, Xinliang Fu, and Wei Li. "Synthesis of Spiro Thiazolo[3,2-a]Pyrimidine-Tetrahydrothiophenes via Sulfa-Michael/Aldol Cascade Reactions." Journal of Chemical Research 41, no. 12 (December 2017): 722–24. http://dx.doi.org/10.3184/174751917x15125690124282.

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The sulfa-Michael/aldol cascade reaction of 2-arylmethylidene-6,7-dihydro-2 H-thiazolo[3,2- a]pyrimidin-3(5 H)-ones and 1,4-dithiane-2,5-diol afforded novel 2′-aryl-4′-hydroxy-4′,5′,6,7-tetrahydro-2′ H-spiro[thiazolo[3,2- a]pyrimidine-2,3′-thiophen]-3(5 H)-ones in good yields. The structures of all products were characterised thoroughly by NMR, IR, HRMS, together with X-ray crystallographic analysis.

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17

Liu, Renzhi, Qihong Mei, Yan Shen, Yiqiang Wu, and Wenlin Xie. "Solvent-free Synthesis of Novel Spirocyclic Oxindole Derivatives via a Michael-Aldol Cascade by Grinding." Journal of Chemical Research 42, no. 5 (May 1, 2018): 244–46. http://dx.doi.org/10.3184/174751918x15260499526233.

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A simple and novel synthesis of spirocyclic oxindole derivatives by the reaction of ( E)-3-arylideneindole-2-ones and 1,4-dithiane-2,5-diol via a Michael-aldol cascade under solvent-free reaction conditions is reported. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4’,5′-dihydro-2' H-spiro[oxindole-3,3′-thiophen]-2-ones in moderate to good yields. The structures of all the products were characterised by NMR, infrared spectroscopy and HRMS.

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18

SUGAWARA, A., R. SUGAWARA, H. ITO, H. TANAKA, T. SEGAWA, and R. SATO. "ChemInform Abstract: A Convenient Synthesis of 1,3-Dithiane Derivatives by Reaction of 4- Methyl-1,3-dithiane-2-thione with Grignard Reagents and Butyllithium." ChemInform 23, no. 2 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199202231.

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19

Lei, Jiaying, Xinliang Fu, Yulin Huang, and Xiaofang Li. "Synthesis of spiro[benzo[4,5]imidazo[2,1-b][1,3]thiazole-2,3-thiolane]s via sulfa-Michael/aldol cascade reactions." Journal of Chemical Research 43, no. 1-2 (January 2019): 63–66. http://dx.doi.org/10.1177/1747519819831898.

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The sulfa-Michael/aldol cascade reaction of ( Z)-2-arylmethylidene-benzo[4,5]imidazo[2,1- b]thiazol-3(2H)-ones and 1,4-dithiane-2,5-diol afforded novel 2-aryl-4-hydroxy-spiro[benzo[4,5]imidazo[2,1- b][1,3]thiazole-2,3-thiolan]-3-ones in moderate yields. The structures of all the products were characterized thoroughly by nuclear magnetic resonance, infrared and high-resolution mass spectrometry together with X-ray crystallographic analysis.

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20

Hogan, Terrence E., Yuan-Yong Yan, William L. Hergenrother, and David F. Lawson. "Lithiated Thiaacetals as Initiators for Living Anionic Polymerization of Diene Elastomers: Polymerization and Compounding." Rubber Chemistry and Technology 80, no. 2 (May 1, 2007): 194–211. http://dx.doi.org/10.5254/1.3539402.

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Abstract Polybutadiene and poly(butadiene-co-styrene) elastomers were prepared in high conversions using 2-lithio-2- methyl-1,3-dithiane as the initiator. Polymers were readily prepared with a polydispersity index (PDI) of 1.05 to 1.26 and a Mn of up to 208 kg/mol. The replacement of the 2-methyl substituent with phenyl, trimethylsilyl or 4-dimethylamino phenyl also gave active initiators that incorporated at the head of the chain. However, initiation rates appeared to vary somewhat with the structure of the initiators. The polymerizations obtained are in all cases controlled and apparently living with the live chain ends capable of further reactions. The initiators could be generated prior to addition to the polymerization mixture or by an in-situ procedure. Model studies gave evidence that the dithiane chain end can be opened under cure conditions and react with unsaturation present in the polymer chain. Several of the product polymers were found to impart improved hysteresis to carbon and silica-filled rubbery vulcanizates possibly through an endlinking mechanism.

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21

Juaristi, Eusebio, Lucia Valle, Bertha A. Valenzuela, and Miguel A. Aguilar. "Sulfur-carbon-phosphorus anomeric interactions. 4. Conformational analysis of 2-(diphenylphosphinoyl)-1,3-dithiane." Journal of the American Chemical Society 108, no. 8 (April 1986): 2000–2005. http://dx.doi.org/10.1021/ja00268a045.

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22

Young, Charles G., Brian R. James, and Steven J. Rettig. "The synthesis and characterization of 3,3-disubstituted pent-4-enals and their 2,2-(trimethylenedithio)pent-4-enal precursors, including the X-ray crystal structure of (R)-3-ethyl-3-phenyl-2,2-(trimethylenedithio)pent-4-enal." Canadian Journal of Chemistry 63, no. 5 (May 1, 1985): 1035–40. http://dx.doi.org/10.1139/v85-176.

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A variety of 3,3-disubstituted pent-4-enals (5a, R = Me, R′ = Et; 5b, R = Me, R′ = Ph; 5c, R = Et, R′ = Ph) has been prepared by the Raney nickel desulfurization of the corresponding 3,3-disubstituted 2,2-(trimethylenedithio)pent-4-enal precursors 4a–4c. The precursor compounds were prepared by the alkylation of 2-formyl-1,3-dithiane with the appropriate 3,3-disubstituted allylic bromide. The new compounds have been characterized by elemental analysis, infrared and nmr spectroscopy, and mass spectrometry. The crystal and molecular structure of (R)-4c has also been determined by X-ray crystallography. At temperatures of ca. 130 °C, compounds 4a–4c undergo intramolecular rearrangement to form the tri-substituted alkenes 6a–6c, which have also been characterized by the present study.

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23

Balachandran, Kalpana, Nanthini Raveendiran, and Margaret Marie John. "1, 4 Dithiane 2, 5 Diol : An Versatile Monomer to Synthesis Aliphatic Random Copolyester with Biomedical Application." Oriental Journal of Chemistry 35, no. 2 (April 28, 2019): 885–91. http://dx.doi.org/10.13005/ojc/350253.

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This article uses 1, 4-dithiane-2, 5-diol as a monomer to synthesize aliphatic random copolyester (PDDD).PDDD was synthesized by direct melt polycondensation method and characterized by FT-IR and 1H- NMR. The physical properties of PDDD were characterized by X-ray diffraction, differential scanning calorimetry, as well as viscosity and solubility measurements. The anticancer, antioxidant, and antimicrobial activity of PDDD were evaluated to investigate its potential biomedical applications. Generally, good results were obtained. It is evident that the copolyester exhibits favorable and tunable physical, thermal and biological properties and so is a suitable candidate for biomedical applications.

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24

Weston, John B., John P. Larkin, David A. Pulman, Ian Holden, and John E. Casida. "Insecticidal isomers of 4-tert-butyl-1-(4-ethynylcyclohexyl)-2,6,7-trioxabicyclo [2.2.2] octane and 5-tert-butyl-2-(4-ethynylcyclohexyl)-1,3-dithiane." Pesticide Science 44, no. 1 (May 1995): 69–74. http://dx.doi.org/10.1002/ps.2780440110.

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25

Suzuki, Yasuo, Yasuhiro Nakamura, Shinji Ando, and Mitsuru Ueda. "Synthesis of Highly Refractive Polyimides Derived from 2,5-Bis(4-aminophenylsulfanyl)-1,4-dithiane and Dianhydrides." Journal of Photopolymer Science and Technology 21, no. 1 (2008): 131–36. http://dx.doi.org/10.2494/photopolymer.21.131.

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26

Li, Xuehe, Yong-Woon Jung, Scott E. Snyder, Joseph Blair, Philip S. Sherman, Timothy Desmond, Kirk A. Frey, and Michael R. Kilbourn. "5-tert-Butyl-2-(4′-[18F]fluoropropynylphenyl)-1,3-dithiane oxides: potential new GABAA receptor radioligands." Nuclear Medicine and Biology 35, no. 5 (July 2008): 549–59. http://dx.doi.org/10.1016/j.nucmedbio.2007.08.003.

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27

Dölling, Wolfgang, Klaus Frost, Frank Heinemann, and Helmut Hartung. "Reaktionen von Derivaten der (Diphenylmethylen-amino)-essigsäure mit Schwefelkohlenstoff und Phenylisothiocyanat sowie Kristall- und Molekülstruktur des 2-(Diphenylmethylen-amino)-2-(1,3-dithian-2-yliden)-essigsäuremethylesters / Reactions of the Derivatives of (Diphenylmethylene-amino) Acetic Acid with Carbon Disulfide and Phenyl Isothiocyanate and Crystal and Molecular Structure of Methyl 2-(Diphenylmethylene-amino)-2-(1,3-dithiane-2-ylidene) Acetate." Zeitschrift für Naturforschung B 48, no. 4 (April 1, 1993): 493–504. http://dx.doi.org/10.1515/znb-1993-0416.

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Derivatives of (diphenylmethylene-amino) acetic acid 1-3 react in the presence of bases (NaH, t-BuONa) or under phase transfer conditions with carbon disulfide to give the corresponding ketene dithioacetals 4-11 after alkylation. Phenyl isothiocyanate and dicyclohexyl carbodiimide give rise to ketene-S,N- and N,N-acetals. Methyl 2-(diphenylmethyleneamino)-2-(1,3-dithiane-2-ylidene) acetate (7) was characterized by an X-ray structure determination. The compound has a 2-aza-1,3-butadiene fragment containing two well localized double bonds. The C=N-C=C group is significantly non-planar, the relevant torsion angle amounts to -103.5(3)°.

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28

Ahluwalia, V. K., and Suman Dudeja. "A CONVENIENT SYNTHESIS OF 1,3-DISUBSTITUTED-4-(1′,3′-DITHIOLANE/DITHIANE-2′-YLIDENE)-2-PYRAZOLIN-5-ONES." Synthetic Communications 31, no. 20 (January 2001): 3175–81. http://dx.doi.org/10.1081/scc-100105894.

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29

Luna, Isadora Silva, Rayssa Marques Duarte da Cruz, Ryldene Marques Duarte da Cruz, Rodrigo Santos Aquino de Araújo, and Francisco Jaime Bezerra Mendonça-Junior. "1,4-Dithiane-2,5-diol: A Versatile Synthon for the Synthesis of Sulfur-containing Heterocycles." Current Organic Synthesis 15, no. 8 (December 17, 2018): 1026–42. http://dx.doi.org/10.2174/1570179415666180821154551.

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Background: 1,4-Dithiane-2,5-diol (1,4-DTD) is the stable dimer of α-mercapto acetaldehyde. This commercially available ambidentade compound is characterized as having in its chemical structure one group that acts as an electrophile and another that acts as a nucleophile, this permits its use as versatile and efficient synthon in synthetic heterocycle procedures. Objective: The aim of this review is to present synthetic applications of 1,4-DTD in heterocyclic chemistry and their applicability to the synthesis of bioactive compounds. Conclusion: Gewald reactions to obtain C-4 and C-5 unsubstituted 2-amino-thiophene derivatives; sulfa- Michael/Henry and sulfa-Michael/aldol sequences to obtain polysubstituted tetrahydrothiophenes, and other heterocyclic reactions that allow synthesizing several functionalized sulfur-containing heterocycles such as thiazolidines, oxathiazinoles and thiazoles are presented and discussed. The use of such heterocyclics in subsequent reactions allows obtaining various bioactive compounds including the antiretroviral lamivudine which is one of the examples presented in this review.

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30

Ribeiro, Douglas S., and Roberto Rittner. "The conformational energies of 2-methyl- and 4-methyl-1,3-dithiane. The breakdown of 1,3-syn diaxial repulsion hypothesis." Journal of Molecular Structure 657, no. 1-3 (September 2003): 85–92. http://dx.doi.org/10.1016/s0022-2860(03)00357-0.

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31

Ahluwalia, V. K., and Suman Dudeja. "ChemInform Abstract: A Convenient Synthesis of 1,3-Disubstituted-4- (1′,3′-dithiolane/dithiane-2′-ylidene)-2-pyrazolin-5-ones." ChemInform 33, no. 3 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200203133.

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32

Fournet, Guy, and Jacques Goré. "Ring enlargement of 2-Oxo-1,3-dithiane : Easy access to 4-substituted-7,8-dihydro-2H,6H-1,5-dithiocin-2-one." Tetrahedron Letters 34, no. 44 (October 1993): 7057–58. http://dx.doi.org/10.1016/s0040-4039(00)61596-4.

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33

Mei, Xinyi, Wendy Zhao, Qiang Ma, Zheng Yue, Hamza Dunya, Qianran He, Amartya Chakrabarti, Christopher McGarry, and Braja K. Mandal. "Solid Polymer Electrolytes Derived from Crosslinked Polystyrene Nanoparticles Covalently Functionalized with a Low Lattice Energy Lithium Salt Moiety." ChemEngineering 4, no. 3 (July 16, 2020): 44. http://dx.doi.org/10.3390/chemengineering4030044.

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Three new crosslinked polystyrene nanoparticles covalently attached with low lattice energy lithium salt moieties were synthesized: poly(styrene lithium trifluoromethane sulphonyl imide) (PSTFSILi), poly(styrene lithium benzene sulphonyl imide) (PSPhSILi), and poly(styrene lithium sulfonyl-1,3-dithiane-1,1,3,3-tetraoxide) (PSDTTOLi). A series of solid polymer electrolytes (SPEs) were formulated by mixing these lithium salts with high molecular weight poly(ethylene oxide), poly(ethylene glycol dimethyl ether), and lithium bis(fluorosulfonyl)imide. The crosslinked nano-sized polymer salts improved film strength and decreased the glass transition temperature (Tg) of the polymer electrolyte membranes. An enhancement in both ionic conductivity and thermal stability was observed. For example, the SPE film containing PSTFSILi displayed ionic conductivity of 7.52 × 10−5 S cm−1 at room temperature and 3.0 × 10−3 S cm−1 at 70 °C, while the SPE film containing PSDTTOLi showed an even better performance of 1.54 × 10−4 S cm−1 at room temperature and 3.23 × 10−3 S cm−1 at 70 °C.

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34

DuPriest, Mark T., and Billie M. York. "Method for treating hypertension with 2,3-diamino-1,4-butanedithiol; 4, 5-diamino-1,2-dithiane; and N-acyl and N-alkyl derivatives thereof." International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology 15, no. 1 (January 1988): ii. http://dx.doi.org/10.1016/0883-2897(88)90173-0.

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35

FOURNET, G., and J. GORE. "ChemInform Abstract: Ring Enlargement of 2-Oxo-1,3-dithiane: Easy Access to 4-Substituted 7, 8-Dihydro-2H,6H-1,5-dithiocin-2-one." ChemInform 25, no. 5 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199405200.

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36

Chen, Binhui, Hangcheng Ni, Xiao Guo, Guolin Zhang, and Yongping Yu. "Facile preparation of 3,5-disubstituted-4-aminothiophene-2-carbaldehyde from a novel unexpected domino reaction of vinyl azides and 1,4-dithiane-2,5-diol." RSC Adv. 4, no. 84 (2014): 44462–65. http://dx.doi.org/10.1039/c4ra08649j.

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37

Kapfer, Isabelle, Jon E. Hawkinson, John E. Casida, and Maurice P. Goeldner. "Photoactivatable 2-[(4'-azido)tetrafluorophenyl]-5-tert-butyl-1,3-dithiane bissulfone and related compounds as candidate irreversible probes for the GABA-gated chloride channels." Journal of Medicinal Chemistry 37, no. 1 (January 1994): 133–40. http://dx.doi.org/10.1021/jm00027a016.

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38

Harlow, Richard L., Allen G. Oliver, Jonathan M. Baker, William J. Marshall, and Michael P. Sammes. "Comparison of the C—H...O bonding in two crystalline phases of 1,4-dithiane 1,1,4,4-tetraoxide." Acta Crystallographica Section E Crystallographic Communications 75, no. 5 (April 5, 2019): 576–79. http://dx.doi.org/10.1107/s2056989019004407.

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The crystal structures of two crystalline phases of 1,4-dithiane 1,1,4,4-tetraoxide, C4H8O4S2, have been determined in order to examine the nature of possible intermolecular hydrogen bonds. Phase 1 is monoclinic, space group C2/m, with unit-cell dimensions of a = 9.073 (8), b = 7.077 (6), c = 5.597 (5) Å and β = 105.89 (1)°. The molecule adopts 2/m symmetry and all of the molecules are related by translation and thus have the same orientation. Phase 2 is also monoclinic but in space group P21/n with unit-cell dimensions of a = 7.1305 (5), b = 5.7245 (4), c = 8.3760 (6) Å and β = 91.138 (2)°. In this phase, the molecule sits on an inversion center and the molecules within the unit cell adopt quite different orientations. In both phases, examination of the potential C—H...O hydrogen bonds around each of the independent oxygen atoms (one axial and the other equatorial) shows the general O...H patterns to be quite similar with each oxygen atom in contact with four neighboring H atoms, and each H atom contacting two neighboring O atoms. While none of the H...O contacts is particularly short (all are greater than 2.5 Å), each molecule has 32 such contacts that form an extensive intermolecular network. A 1H NMR spectrum of the compound dissolved in DMSO shows a singlet of 8H at δ 3.677 which indicates that the C—H bonds are only moderately polarized by the single adjacent –SO2– moiety: strongly polarized C—H bonds have δ values in the 5–6 range [Li & Sammes (1983). J. Chem. Soc. Perkin Trans. 1, pp. 1303–1309]. The phase 1 crystal studied was non-merohedrally twinned.

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39

Chen, Binhui, Hangcheng Ni, Xiao Guo, Guolin Zhang, and Yongping Yu. "ChemInform Abstract: Facile Preparation of 3,5-Disubstituted-4-aminothiophene-2-carbaldehyde from a Novel Unexpected Domino Reaction of Vinyl Azides and 1,4-Dithiane-2,5-diol." ChemInform 46, no. 13 (March 2015): no. http://dx.doi.org/10.1002/chin.201513160.

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40

KAPFER, I., J. E. HAWKINSON, J. E. CASIDA, and M. PH GOELDNER. "ChemInform Abstract: Photoactivatable 2-(4′-Azidotetrafluorophenyl)-5-tert-butyl-1,3- dithiane-Bis-sulfone and Related Compounds as Candidate Irreversible Probes for the GABA-Gated Chloride Channels." ChemInform 25, no. 17 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199417178.

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41

Kapon, M., and F. H. Herbstein. "Disorder and not incipient reaction is the cause of the anomalies in the crystal structure of trans-4-chloro-2,4,6-tris(trichloromethyl)-1-oxa-3,5-dithiane." Acta Crystallographica Section B Structural Science 51, no. 1 (February 1, 1995): 108–13. http://dx.doi.org/10.1107/s0108768194007482.

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42

Fabian, Jürgen, and Peter Birner. "A theoretical study of the disulfide/dithione valence isomerism." Collection of Czechoslovak Chemical Communications 53, no. 9 (1988): 2096–115. http://dx.doi.org/10.1135/cccc19882096.

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According to MNDO calculations on 1,2-dithiete (IIIa), 1,2-dithiin (IVa) and 3,4-dimethylene-1,2-dithiane (Va) the closed-ring compounds are thermodynamically more stable than the open-chain compounds whereas the reverse holds for 4-methylene-1,2-dithiole (VIa). Substitution of the exocyclic CH2 group of VIa by O, S, NH, and OH+ stabilizes its cyclic mesoionic structure. The low triplet state energy of VIa and of some derivatives relative to the lowest singlet state energy signalizes the biradicaloid nature of these electronic structures. Replacement of hydrogen of the methine groups adjacent to sulfur of III, IV, and VII by CH3, CF3, C6H5, CHO or CN results more or less in stabilization of the cyclic tautomer whereas donor substituents such as NH2, OCH3 or SCH3 act less uniformly but mostly in a destabilizing way. Contrary to former assumptions, there is no indication for a species intermediate between the disulfide and dithione structure that defines the molecular ground state. A relatively low ground state barrier separates the two isomeric structures although thermal isomerization of IIIa belongs to Woodward-Hoffmann forbidden concerted reactions (calculated activation energy for the ring opening of IIIa about 36 kcal/mol). The thermal and photochemical isomerization is discussed in terms of the change of the energy along the reaction path of the closed shell ground state (S0) and lowest energy excited states (S1, T1). The energies are obtained by MNDO, MNDO/2 x 2 CI, MNDO/HE, and MNDO/HE/3 x 3 CI calculations.

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43

Irving, Anne, and Harry M. N. H. Irving. "Isomerism in some 1-oxa-3,5-dithians and the X-ray structure determination of 2,6-bis(trichloromethyl)-4-dichloromethylene-1-oxa-3,5-dithian." Journal of Crystallographic and Spectroscopic Research 16, no. 6 (December 1986): 851–62. http://dx.doi.org/10.1007/bf01188191.

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44

Ayala, J. D., G. Bombieri, A. Del Pra, A. Fantoni, and G. Vicentini. "Different picrate coordination modes along the lanthanide series: synthesis and molecular structure of two isomorphous compounds [Ln2(pic)4(TDTD)3(H2O)2](pic)2(H2O)2 (Ln = Tm, Lu; pic = picrate; TDTD = trans-1,4-dithiane,S,S′-dioxide)." Inorganica Chimica Acta 274, no. 1 (June 1998): 122–25. http://dx.doi.org/10.1016/s0020-1693(97)06040-4.

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45

Bertini, Vincenzo, Francesco Lucchesini, Marco Pocci, and Angela De Munno. "1,3-Dithiane polymers for the supported synthesis of ketones." Tetrahedron Letters 39, no. 50 (December 1998): 9263–66. http://dx.doi.org/10.1016/s0040-4039(98)02081-4.

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46

Fink, H., and I. Stahl. "Konformation von 2-Methyl-2-(4-nitrophenyl)-1,3-dithian, C11H13NO2S2." Acta Crystallographica Section C Crystal Structure Communications 41, no. 1 (January 15, 1985): 151–53. http://dx.doi.org/10.1107/s0108270185003109.

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47

Griera, Rosa, Lluis Rigat, Mercedes Alvarez, and John A. Joule. "Reactions of 1-methyl-4-quinolone with 2-lithio-1,3-dithianes." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1992): 1223. http://dx.doi.org/10.1039/p19920001223.

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48

Hussain, Z., F. F. Fleming, R. E. Norman, and S. C. Chang. "3-Cyano-1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine." Acta Crystallographica Section C Crystal Structure Communications 52, no. 4 (April 15, 1996): 1010–12. http://dx.doi.org/10.1107/s010827019501345x.

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49

Zhu, Chao-Guang, Dong-Sheng Zhu, Xiao-Yan Wu, Yan-Hua Wang, and Da-Feng Du. "(Z)-Methyl 2-(1,3-dithian-2-ylidene)-4-(triphenylstannyl)but-3-enoate." Acta Crystallographica Section E Structure Reports Online 63, no. 9 (August 15, 2007): m2346. http://dx.doi.org/10.1107/s160053680703961x.

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50

Wood, P. N., and B. M. Fisher. "The effect of fungicides on spore germination, mycelial growth and lesion development of Phlyctema vagabunda (syn: Neofabraea alba) (bull’s eye rot of apples)." New Zealand Plant Protection 70 (August 8, 2017): 112–19. http://dx.doi.org/10.30843/nzpp.2017.70.36.

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Phlyctema vagabunda (syn: Neofabraea alba) is a plant pathogenic fungus that causes bull’s eye rot on apples and pears. Phlyctema vagabunda fruit infections occur in orchards predominantly pre-harvest, and eventually express as a fruit rot after 4—5 months of cool storage. Twelve fungicides (captan, carbendazim, copper hydroxide, cyprodinil, difenoconazole, dithianon, dodine, isopyrazam, metiram, lime sulphur, sulphur and trifloxystrobin) were tested in vitro for their effects on spore germination and mycelial growth of P. vagabunda. Spore germination was inhibited by metiram, captan, dodine, dithianon, lime sulphur, carbendazim and isopyrazam, in order of effectiveness. Carbendazim, isopyrazam, difenoconazole and cyprodinil, in order of effectiveness, inhibited mycelial growth when used at label rates. Wettable sulphur was ineffective in both assays. On detached apple fruit, carbendazim, cyprodinil, trifloxystrobin and isopyrazam (in order of effectiveness) inhibited lesion development.

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