Home Tellurium-induced cyclization of olefinic compounds
Article
Licensed
Unlicensed Requires Authentication

Tellurium-induced cyclization of olefinic compounds

  • Sara Ali A Aldawood , Aparna Das ORCID logo and Bimal Krishna Banik EMAIL logo
Published/Copyright: May 17, 2022
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Physical Sciences Reviews
From the journal Physical Sciences Reviews Volume 8 Issue 12

Abstract

In this article, we discuss about the importance of Tellurium (Te) in organic synthesis. Tellurium-induced cyclization of alkenyl compounds, as well as alkynyl compounds, are considered for the study. The developments in this area are incorporated in great detail. The mechanism of the reactions does not follow any straightforward process. This study opens up the possibility of stereocontrolled synthesis of complex natural products.

Keywords: alkenyl compounds; alkynyl compounds; cyclization; olefinic compounds; tellurium
Corresponding author: Bimal Krishna Banik, Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Prince Mohammad Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia, E-mail:

Acknowledgements

BKB and AD are thankful to Prince Mohammad Bin Fahd University for support.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Harmange, J-C, Figadère, B. Synthetic routes to 2,5-disubstituted tetrahydrofurans. Tetrahedron Asymmetry 1993;4:1711–54. https://doi.org/10.1016/s0957-4166(00)80408-5.Search in Google Scholar

2. Lee, YY, Kim, BH. Total synthesis of nonactin. Tetrahedron 1996;52:571–88. https://doi.org/10.1016/0040-4020(95)00913-2.Search in Google Scholar

3. Solladie, G, Dominguez, C. A short asymmetric synthesis of (+)-Nonactic acid and (−)-8-epi-Nonactic acid induced by a chiral sulfoxide group. J Org Chem 1994;59:3898–901. https://doi.org/10.1021/jo00093a022.Search in Google Scholar

4. Lygo, B. Stereoselective synthesis of (±)-methyl homononactate and (±)-methyl 8-epi-homononactate. Tetrahedron 1988;44:6889–96. https://doi.org/10.1016/s0040-4020(01)86218-9.Search in Google Scholar

5. Bartlett, PA, Meadows, JD, Ottow, E. Enantiodivergent syntheses of dextro nonactic acid and levo nonactic acid and the total synthesis of nonactin. J Am Chem Soc 1984;106:5304–11. https://doi.org/10.1021/ja00330a045.Search in Google Scholar

6. Jackson, WP, Ley, SV, Morton, JA. Cyclisation reactions of alkenyl β-ketoesters involving a novel phenylseleno group migration. Tetrahedron Lett 1981;22:2601–4. https://doi.org/10.1016/s0040-4039(01)90531-3.Search in Google Scholar

7. Antonioletti, R, Bonadies, F, Scettri, A. A convenient approach to furan derivatives by I2-induced cyclisation of 2-alkenyl substituted 1,3-dicarbonyl compounds. Tetrahedron Lett 1988;29:4987–90. https://doi.org/10.1016/s0040-4039(00)80660-7.Search in Google Scholar

8. Antonioletti, R, Cecchini, C, Ciani, B, Magnanti, S. Iodoenolcyclization. III. A general approach to tetrasubstituted furans from 2-alkenyl-1,3-dicarbonyl compounds. Tetrahedron Lett 1995;36:9019–22. https://doi.org/10.1016/0040-4039(95)01901-s.Search in Google Scholar

9. Iqbal, J, Pandey, A. A highly regioselective iodoenoletherification of α-Allyl-β-ketoesters. A convenient route to 2-Alkyl-5-iodomethyl-3-methoxycarbonyl-4, 5-dihydrofurans. Synth Commun 1990;20:665–70. https://doi.org/10.1080/00397919008052308.Search in Google Scholar

10. Ferraz, HMC, de Oliveira, EO, Payret-Arrua, ME, Brandt, CA. A new and efficient approach to cyclic .beta.-Enamino esters and .beta.-Enamino ketones by iodine-promoted cyclization. J Org Chem 1995;60:7357–9. https://doi.org/10.1021/jo00127a051.Search in Google Scholar

11. Ferraz, HMC, Sano, MK, Scalfo, AC. Tellurium and iodine promoted cyclofunctionalization of alkenyl substituted β-keto esters. Synlett 1999;1999:567–8. https://doi.org/10.1055/s-1999-2679.Search in Google Scholar

12. Silberman, A, Kalechman, Y, Hirsch, S, Erlich, Z, Sredni, B, Albeck, A. The anticancer activity of organotelluranes: potential role in integrin inactivation. Chembiochem 2016;17:918–27. https://doi.org/10.1002/cbic.201500614.Search in Google Scholar PubMed

13. Piovan, L, Milani, P, Silva, MS, Moraes, PG, Demasi, M, Andrade, LH. 20S proteasome as novel biological target for organochalcogenanes. Eur J Med Chem 2014;73:280–5. https://doi.org/10.1016/j.ejmech.2013.12.011.Search in Google Scholar PubMed

14. El Chamy Maluf, S, Melo, PMS, Varotti, FP, Gazarini, ML, Cunha, RLOR, Carmona, AK. Hypervalent organotellurium compounds as inhibitors of P. falciparum calcium-dependent cysteine proteases. Parasitol Int 2016;65:20–2. https://doi.org/10.1016/j.parint.2015.09.006.Search in Google Scholar PubMed

15. Cunha, RLOR, Gouvêa, IE, Feitosa, GPV, Alves, MFM, Brömme, D, Comasseto, JV, et al.. Irreversible inhibition of human cathepsins B, L, S and K by hypervalent tellurium compounds. Biol Chem 2009;390:1205–12. https://doi.org/10.1515/BC.2009.125.Search in Google Scholar PubMed

16. Cunha, RLOR, Urano, ME, Chagas, JR, Almeida, PC, Bincoletto, C, Tersariol, ILS, et al.. Tellurium-based cysteine protease inhibitors: evaluation of novel organotellurium(IV) compounds as inhibitors of human cathepsin B. Bioorg Med Chem Lett 2005;15:755–60. https://doi.org/10.1016/j.bmcl.2004.11.012.Search in Google Scholar PubMed

17. Halpert, G, Sredni, B. The effect of the novel tellurium compound AS101 on autoimmune diseases. Autoimmun Rev 2014;13:1230–5. https://doi.org/10.1016/j.autrev.2014.08.003.Search in Google Scholar PubMed

18. Tiekink, ERT. Therapeutic potential of selenium and tellurium compounds: opportunities yet unrealised. Dalton Trans 2012;41:6390–5. https://doi.org/10.1039/c2dt12225a.Search in Google Scholar PubMed

19. Cunha, RLOR, Gouvea, IE, Juliano, L. A glimpse on biological activities of tellurium compounds. An Acad Bras Cienc 2009;81:393–407. https://doi.org/10.1590/s0001-37652009000300006.Search in Google Scholar PubMed

20. Comasseto, JV, Ferraz, HMC, Petragnani, N, Brandt, CA. Cyclofunctionalization of unsaturated alcohols with aryltellurium trihalides. Tetrahedron Lett 1987;28:5611–4. https://doi.org/10.1016/s0040-4039(00)96793-5.Search in Google Scholar

21. Comasseto, JV, Grazini, MVA. Cyclization of olefinic benzyl ethers with aryltellurium trichlorides. Synth Commun 1992;22:949–54. https://doi.org/10.1080/00397919208020859.Search in Google Scholar

22. Comasseto, JV, Petragnani, N. Cyclofunctionalization with aryltellurium trichlorides. Synth Commun 1983;13:889–99. https://doi.org/10.1080/00397918308059542.Search in Google Scholar

23. Ferraz, HM, Comasseto, JV, de Borba, EB. Telurociclofuncionalizaqao de compostos 2-alquenil 1,3-dicarbonilicos. Quim Nova 1992;15:298.Search in Google Scholar

24. Ferraz, HMC, Sano, MK, Nunes, MRS, Bianco, GG. Synthesis of cyclic enol ethers from alkenyl-β-dicarbonyl compounds. J Org Chem 2002;67:4122–6. https://doi.org/10.1021/jo011089+.10.1021/jo011089+Search in Google Scholar PubMed

25. Stefani, HA, Petragnani, N, Brandt, CA, Rando, DG, Valduga, CJ. Seleno and telluro cyclofunctionalization of α,γ-diallyl-β-ketoesters: polysubstituted furan derivatives. Synth Commun 1999;29:3517–31. https://doi.org/10.1080/00397919908085985.Search in Google Scholar

26. Kut, M, Fizer, M, Onysko, M, Lendel, V. Reactions of N-alkenyl thioureas with p-alkoxyphenyltellurium trichlorides. J Heterocycl Chem 2018;55:2284–90. https://doi.org/10.1002/jhet.3281.Search in Google Scholar

27. Kut, V, Onysko, V, Lendel, V, Mykola, K. Electrophile cyclization of N(S, Se)-alkenyl derivatives of pyrimidinone with p-metoxyphenyltellurium trichloride. Sci Bull Uzhhorod Univ Chem Ser 2019;42:63–72. https://doi.org/10.24144/2414-0260.2019.2.63-72.Search in Google Scholar

28. Petragnani, N, Comasseto, JV.Tellurium reagents in organic synthesis: recent advances. Part 2. Synthesis 1991;1991:897–919. https://doi.org/10.1055/s-1991-26605.Search in Google Scholar

29. Campos, MDM, Petragnani, N. Nachbargruppenbeteiligung bei additionsreaktionen, IV. Darstellung von α.α-disubstituierten δ-arylselenenyl-und δ-aryltelluro-γ-valerolactonen. Chem Ber 1960;93:317–20. https://doi.org/10.1002/cber.19600930207.Search in Google Scholar

30. Wirth, T, Häuptli, S, Leuenberger, M. Catalytic asymmetric oxyselenenylation–elimination reactions using chiral selenium compounds. Tetrahedron Asymmetry 1998;9:547–50. https://doi.org/10.1016/s0957-4166(98)00031-7.Search in Google Scholar

31. Moraes, DN, Santos, RA, Comasseto, JV. The influence of the substrate structure in the tellurocyclofunctionalization reaction of g,d-unsaturated carboxylic acids and their corresponding benzyl esters. J Braz Chem Soc 1998;9:397–403. https://doi.org/10.1590/s0103-50531998000400013.Search in Google Scholar

32. Yoshida, M, Suzuki, T, Kamigata, N. Novel preparation of highly electrophilic species for benzenetellurenylation or benzenesulfenylation by nitrobenzenesulfonyl peroxide in combination with ditelluride or disulfide. Application to intramolecular ring closures. J Org Chem 1992;57:383–6. https://doi.org/10.1021/jo00027a068.Search in Google Scholar

33. Hu, NX, Aso, Y, Otsubo, T, Ogura, F. Cyclofunctionalization of hydroxyolefins induced by arenetellurinic anhydride. Tetrahedron Lett 1987;28:1281–4. https://doi.org/10.1016/s0040-4039(00)95346-2.Search in Google Scholar

34. Hu, NX, Aso, Y, Otsubo, T, Ogura, F. Cyclofunctionalization of hydroxy olefins induced by arenetellurinyl acetate. J Org Chem 1989;54:4391–7. https://doi.org/10.1021/jo00279a030.Search in Google Scholar

35. Hu, NX, Aso, Y, Otsubo, T, Ogura, F. Organotellurium-mediated synthesis of oxazolidin-2-ones from alkenes. J Chem Soc Chem Commun 1987;1447–8. https://doi.org/10.1039/c39870001447.Search in Google Scholar

36. Hu, NX, Aso, Y, Otsubo, T, Ogura, F. Organotelluriums. 20. Aminotellurinylation of olefins and its utilization for synthesis of 2-oxazolidinones. J Org Chem 1989;54:4398–404. https://doi.org/10.1021/jo00279a031.Search in Google Scholar

37. Hu, NX, Aso, Y, Otsubo, T, Ogura, F. Tellurium-based organic synthesis: a novel one-pot formation of 2-oxazolines from alkenes induced by amidotellurinylation. Tetrahedron Lett 1988;29:1049–52. https://doi.org/10.1016/0040-4039(88)85332-2.Search in Google Scholar

38. Hu, NX, Aso, Y, Otsubo, T, Ogura, F. Organotelluriums. Part 21. Amidotellurinylation of olefins and a novel one-pot synthesis of 4,5-dihydro-oxazoles from olefins. J Chem Soc Perkin 1989;1:1775–80. https://doi.org/10.1039/p19890001775.Search in Google Scholar

39. Fukumoto, T, Aso, Y, Otsubo, T, Ogura, F. Stereoselective addition reactions of alkynes with benzenetellurinyl trifluoromethanesulfonate in acetonitrile: organotellurium-mediated one-pot synthesis of oxazoles from internal alkynes. J Chem Soc Chem Commun 1992;1070–2. https://doi.org/10.1039/c39920001070.Search in Google Scholar

40. Fukumoto, T, Aso, Y, Otsubo, T, Ogura, F. Syntheses of β-amidovinyltellurides and oxazoles by addition reactions of alkynes with benzenetellurinyl trifluoromethanesulfonate in acetonitrile. Heteroat Chem 1993;4:511–6. https://doi.org/10.1002/hc.520040517.Search in Google Scholar

41. Brill, WF. A site isolated tellurium oxidation catalyst having no soluble analog. J Org Chem 1986;51:1149–50. https://doi.org/10.1021/jo00357a046.Search in Google Scholar

42. Alberto, EE, Muller, LM, Detty, MR. Rate accelerations of bromination reactions with NaBr and H2O2 via the addition of catalytic quantities of diaryl ditellurides. Organometallics 2014;33:5571–81. https://doi.org/10.1021/om500883f.Search in Google Scholar

43. Oba, M, Endo, M, Nishiyama, K, Ouchi, A, Ando, W. Photosensitized oxygenation of diaryl tellurides to telluroxides and their oxidizing properties. Chem Commun 2004;35:1672–3. https://doi.org/10.1039/b403683b.Search in Google Scholar PubMed

44. Oba, M, Okada, Y, Nishiyama, K, Ando, W. Aerobic photooxidation of phosphite esters using diorganotelluride catalysts. Org Lett 2009;11:1879–81. https://doi.org/10.1021/ol900240s.Search in Google Scholar PubMed

45. Okada, Y, Oba, M, Arai, A, Tanaka, K, Nishiyama, K, Ando, W. Diorganotelluride-catalyzed oxidation of silanes to silanols under atmospheric oxygen. Inorg Chem 2010;49:383–5. https://doi.org/10.1021/ic9022745.Search in Google Scholar PubMed

46. Oba, M, Tanaka, K, Nishiyama, K, Ando, W. Aerobic oxidation of thiols to disulfides catalyzed by diaryl tellurides under photosensitized conditions. J Org Chem 2011;76:4173–7. https://doi.org/10.1021/jo200496r.Search in Google Scholar PubMed

47. Oba, M, Okada, Y, Endo, M, Tanaka, K, Nishiyama, K, Shimada, S, et al.. Formation of diaryl telluroxides and tellurones by photosensitized oxygenation of diaryl tellurides. Inorg Chem 2010;49:10680–6. https://doi.org/10.1021/ic101708y.Search in Google Scholar PubMed

48. Meinwald, J. Modern synthetic reactions. J Chem Educ 1965;42:A910. https://doi.org/10.1021/ed042pa910.Search in Google Scholar

49. Bartlett, PA, Richardson, DP, Myerson, J. Electrophilic lactonization as a tool in acyclic stereocontrol. Synthesis of serricornin. Tetrahedron 1984;40:2317–27. https://doi.org/10.1016/0040-4020(84)80015-0.Search in Google Scholar

50. Gyu Kim, Y, Cha, JK. Stereoselective synthesis of hydroxy-substituted tetrahydrofurans. Tetrahedron Lett 1988;29:2011–3. https://doi.org/10.1016/s0040-4039(00)87821-1.Search in Google Scholar

51. Cardillo, G, Orena, M. Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates. Tetrahedron 1990;46:3321–408. https://doi.org/10.1016/s0040-4020(01)81510-6.Search in Google Scholar

52. Ley, SV, Lygo, B, Molines, H, Morton, JA. Synthesis of (cis-6-methyltetrahydropyran-2-yl)acetic acid involving the use of an organoselenium-mediated cyclization reaction. J Chem Soc Chem Commun 1982;1251–2. https://doi.org/10.1039/c39820001251.Search in Google Scholar

53. Minami, I, Yuhara, M, Watanabe, H, Tsuji, J. A new furan annelation reaction by the palladium-catalyzed reaction of 2-alkynyl carbonates or 2-(1-alkynyl)oxiranes with β-keto esters. J Organomet Chem 1987;334:225–42. https://doi.org/10.1016/0022-328x(87)80052-9.Search in Google Scholar

54. Tiecco, M, Testaferri, L, Tingoli, M, Bartoli, D, Balducci, R. Ring-closure reactions initiated by the peroxydisulfate ion oxidation of diphenyl diselenide. J Org Chem 1990;55:429–34. https://doi.org/10.1021/jo00289a010.Search in Google Scholar

55. Bergman, J, Engman, L. Oxidative cyclization of some .gamma.- and .delta.-hydroxy olefins induced by tellurium dioxide. J Am Chem Soc 1981;103:5196–200. https://doi.org/10.1021/ja00407a041.Search in Google Scholar

56. Engman, L. Alkoxytellurination of olefins for the preparation of bis (.beta.-alkoxyalkyl) ditellurides and (.beta.-alkoxyalkyl) tellurium trichlorides. Organometallics 1989;8:1997–2000. https://doi.org/10.1021/om00110a026.Search in Google Scholar

57. Comasseto, JV, Ferraz, HMC, Brandt, CA, Gaeta, KK. Reduction of tellurium – carbon bonds of tellurolactones and telluroethers. Tetrahedron Lett 1989;30:1209–12. https://doi.org/10.1016/s0040-4039(00)72717-1.Search in Google Scholar

58. Ohe, K, Takahashi, H, Uemura, S, Sugita, N. Carbonylation of aryl- and vinyl-tellurium compounds with carbon monoxide in the presence of palladium(II) salts. J Organomet Chem 1987;326:35–47. https://doi.org/10.1016/0022-328x(87)80121-3.Search in Google Scholar

59. Ohe, K, Takahashi, H, Uemura, S, Sugita, N. Palladium(II) chloride catalyzed carbonylation of organic tellurides with carbon monoxide. J Org Chem 1987;52:4859–63. https://doi.org/10.1021/jo00231a007.Search in Google Scholar

60. Clive, DLJ, Anderson, PC, Moss, N, Singh, A. New method for coupling allylic halides: use of telluride(2-) ion species. J Org Chem 1982;47:1641–7. https://doi.org/10.1021/jo00348a006.Search in Google Scholar

61. Barton, DH, Ramesh, M. Tandem nucleophilic and radical chemistry in the replacement of the hydroxyl group by a carbon-carbon bond. A concise synthesis of showdomycin. J Am Chem Soc 1990;112:891–2. https://doi.org/10.1021/ja00158a072.Search in Google Scholar

62. Barton, DHR, Ozbalik, N, Sarma, JC. The role of organic tellurides as accumulators and exchangers of carbon radicals. Tetrahedron Lett 1988;29:6581–4. https://doi.org/10.1016/s0040-4039(00)82402-8.Search in Google Scholar

63. Barton, DHR, Dalko, PI, Géro, SD. Preparation of six membered carbocycles by aryl-tellurium mediated free-radical cyclisation. Tetrahedron Lett 1991;32:4713–6. https://doi.org/10.1016/s0040-4039(00)92289-5.Search in Google Scholar

64. Kanda, T, Sugino, T, Kambe, N, Sonoda, N. A new preparative method of organoalkali and organoalkaline-earth metals using metal-tellurium exchange reactions. Phosphorus Sulfur Silicon Relat Elem 1992;67:103–6. https://doi.org/10.1080/10426509208045825.Search in Google Scholar

65. Clive, DLJ, Russell, CG, Chittattu, G, Singh, A. Cyclofunctionalisation of unsaturated acids with benzeneselenenyl chloride: kinetic and thermodynamic aspects of the rules for ring closure. Tetrahedron 1980;36:1399–408. https://doi.org/10.1016/0040-4020(80)85054-x.Search in Google Scholar

66. Nicolaou, KC. Organoselenium-induced cyclizations in organic synthesis. Tetrahedron 1981;37:4097–109. https://doi.org/10.1016/s0040-4020(01)93285-5.Search in Google Scholar

67. Xu, Q, Huang, X, Yuan, J. Facile synthesis of β-organotellurobutenolides via electrophilic tellurolactonization of α-allenoic acids. J Org Chem 2005;70:6948–51. https://doi.org/10.1021/jo050564r.Search in Google Scholar PubMed

68. Macomber, RS, Krudy, GA, Seff, K, Rendon-Diaz-Miron, LE. Sulfur- and selenium-promoted cyclization of allenic phosphonates and phosphinates to substituted 1,2-oxaphosphol-3-enes: stereochemical consequences at phosphorus. The crystal and molecular structure of (Z)-3,5-di-tert-butyl-2-methoxy-4-(phenylseleno)-1,2-oxaphosphol-3-ene 2-oxide. J Org Chem 1983;48:1425–30. https://doi.org/10.1021/jo00157a007.Search in Google Scholar

69. Arnold, RT, Campos, Mde M, Lindsay, KL. Participation of a neighboring carboxyl group in addition reactions. I. The mechanism of the reaction of bromine with γ, δ-unsaturated acids and Esters1. J Am Chem Soc 1953;75:1044–7. https://doi.org/10.1021/ja01101a011.Search in Google Scholar

70. Rowland, RL, Perry, WL, Friedman, HL. Mercurial diuretics. III. Mercuration of allylacetic acid and related compounds. J Am Chem Soc 1951;73:1040–1. https://doi.org/10.1021/ja01147a046.Search in Google Scholar

71. de Moura Campos, M, Petragnani, N. Organic tellurium compounds– IV: vinylic and ethynylic tellurium derivatives. Tetrahedron 1962;18:527–30. https://doi.org/10.1016/s0040-4020(01)92702-4.Search in Google Scholar

72. Adams, R, Roman, FL, Sperry, WN. The structure of the compounds produced from olefins and mercury salts: mercurated dihydrobenzofurans. J Am Chem Soc 1922;44:1781–92. https://doi.org/10.1021/ja01429a024.Search in Google Scholar

73. Leonard, KA, Zhou, F, Detty, MR. Chalcogen(IV)−Chalcogen(II) redox cycles. 1. Halogenation of organic substrates with dihaloselenium(IV) and -tellurium(IV) derivatives. Dehalogenation of vicinal dibromides with diaryl tellurides. Organometallics 1996;15:4285–92. https://doi.org/10.1021/om960476k.Search in Google Scholar

74. Sashida, H, Ito, K, Tsuchiya, T. Synthesis of the first examples of 1-benzotellurepines and 1-benzoselenepines. J Chem Soc Chem Commun 1993;1493–4. https://doi.org/10.1039/c39930001493.Search in Google Scholar

75. Sashida, H, Ito, K, Tsuchiya, T. Studies on seven-membered heterocycles. XXXV. Synthesis of the group 16 1-benzoheteroepines involving the first examples of 1-benzotellurepine and 1-benzoselenepine rings. Chem Pharm Bull 1995;43:19–25. https://doi.org/10.1248/cpb.43.19.Search in Google Scholar

76. Sashida, H, Sadamori, K, Tsuchiya, T. A convenient one-pot preparation of benzo[b]-tellurophenes,-selenophenes, and -thiophenes from o-bromoethynylbenzenes. Synth Commun 1998;28:713–27. https://doi.org/10.1080/00397919808005944.Search in Google Scholar

77. Sashida, H. An alternative facile preparation of telluro- and selenochromones from o-bromophenyl ethynyl ketones. Synthesis 1998;1998:745–8. https://doi.org/10.1055/s-1998-2062.Search in Google Scholar

78. Huang, Z, Lakshmikantham, MV, Lyon, M, Cava, MP. Synthesis and isolation of some benzo[c]tellurophenes. J Org Chem 2000;65:5413–5. https://doi.org/10.1021/jo0001030.Search in Google Scholar PubMed

79. Ziolo, RF, Günther, WHH. The synthesis and characterization of α- and β-1, 1-diiodo-3,4-benzo-1-telluracyclopentane, C8H8Tel2. J Organomet Chem 1978;146:245–51. https://doi.org/10.1016/s0022-328x(00)88751-3.Search in Google Scholar

80. Rajagopal, D, Lakshmikantham, MV, Mørkved, EH, Cava, MP. Generation of the first tellurium-containing diheteropentalene. Org Lett 2002;4:1193–5. https://doi.org/10.1021/ol0256466.Search in Google Scholar PubMed

81. Luo, B, Weng, Z. Elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles using trifluoroacetic anhydride as reagent. Chem Commun 2018;54:10750–3. https://doi.org/10.1039/c8cc05670f.Search in Google Scholar PubMed

Published Online: 2022-05-17

© 2022 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Reviews
  3. Synthesis and application of organotellurium compounds
  4. Tellurium-based chemical sensors
  5. Synthesis of antiviral drugs by using carbon–carbon and carbon–heteroatom bond formation under greener conditions
  6. Green protocols for Tsuji–Trost allylation: an overview
  7. Chemistry of tellurium containing macrocycles
  8. Tellurium-induced cyclization of olefinic compounds
  9. Latest developments on the synthesis of bioactive organotellurium scaffolds
  10. Tellurium-based solar cells
  11. Semiconductor characteristics of tellurium and its implementations
  12. Tellurium based materials for nonlinear optical applications
  13. Pharmaceutical cocrystal consisting of ascorbic acid with p-aminobenzoic acid and paracetamol
  14. Carbocatalysis: a metal free green avenue towards carbon–carbon/heteroatom bond construction
  15. Physico-chemical and nutraceutical properties of Cola lepidota seed oil
  16. Cyclohexane oxidation using advanced oxidation processes with metals and metal oxides as catalysts: a review
  17. Optimization of electrolysis and carbon capture processes for sustainable production of chemicals through Power-to-X
  18. Tellurium-induced functional group activation
  19. Synthesis, characterization, and theoretical investigation of 4-chloro-6(phenylamino)-1,3,5-triazin-2-yl)asmino-4-(2,4-dichlorophenyl)thiazol-5-yl-diazenyl)phenyl as potential SARS-CoV-2 agent
  20. Process intensification and digital twin – the potential for the energy transition in process industries
  21. Photovoltaic properties of novel reactive azobenzoquinolines: experimental and theoretical investigations
  22. Accessing the environmental impact of tellurium metal
  23. Membrane-based processes in essential oils production
  24. Development of future-proof supply concepts for sector-coupled district heating systems based on scenario-analysis
  25. Educators’ reflections on the teaching and learning of the periodic table of elements at the upper secondary level: a case study
  26. Optimization of hydrogen supply from renewable electricity including cavern storage
  27. A short review on cancer therapeutics
  28. The role of bioprocess systems engineering in extracting chemicals and energy from microalgae
  29. The topology of crystalline matter
  30. Characterization of lignocellulosic S. persica fibre and its composites: a review
  31. Constructing a framework for selecting natural fibres as reinforcements composites based on grey relational analysis
  32. Polybutylene succinate (PBS)/natural fiber green composites: melt blending processes and tensile properties
  33. The properties of 3D printed poly (lactic acid) (PLA)/poly (butylene-adipate-terephthalate) (PBAT) blend and oil palm empty fruit bunch (EFB) reinforced PLA/PBAT composites used in fused deposition modelling (FDM) 3D printing
  34. Thermal properties of wood flour reinforced polyamide 6 biocomposites by twin screw extrusion
  35. Manufacturing defects and interfacial adhesion of Arenga Pinnata and kenaf fibre reinforced fibreglass/kevlar hybrid composite in boat construction application
  36. Wettability of keruing (Dipterocarpus spp.) wood after weathering under tropical climate
  37. Simultaneous remediation of polycyclic aromatic hydrocarbon and heavy metals in wastewater with zerovalent iron-titanium oxide nanoparticles (ZVI-TiO2)
https://doi.org/10.1515/psr-2021-0119
Keywords for this article
alkenyl compounds; alkynyl compounds; cyclization; olefinic compounds; tellurium

Articles in the same Issue

  1. Frontmatter
  2. Reviews
  3. Synthesis and application of organotellurium compounds
  4. Tellurium-based chemical sensors
  5. Synthesis of antiviral drugs by using carbon–carbon and carbon–heteroatom bond formation under greener conditions
  6. Green protocols for Tsuji–Trost allylation: an overview
  7. Chemistry of tellurium containing macrocycles
  8. Tellurium-induced cyclization of olefinic compounds
  9. Latest developments on the synthesis of bioactive organotellurium scaffolds
  10. Tellurium-based solar cells
  11. Semiconductor characteristics of tellurium and its implementations
  12. Tellurium based materials for nonlinear optical applications
  13. Pharmaceutical cocrystal consisting of ascorbic acid with p-aminobenzoic acid and paracetamol
  14. Carbocatalysis: a metal free green avenue towards carbon–carbon/heteroatom bond construction
  15. Physico-chemical and nutraceutical properties of Cola lepidota seed oil
  16. Cyclohexane oxidation using advanced oxidation processes with metals and metal oxides as catalysts: a review
  17. Optimization of electrolysis and carbon capture processes for sustainable production of chemicals through Power-to-X
  18. Tellurium-induced functional group activation
  19. Synthesis, characterization, and theoretical investigation of 4-chloro-6(phenylamino)-1,3,5-triazin-2-yl)asmino-4-(2,4-dichlorophenyl)thiazol-5-yl-diazenyl)phenyl as potential SARS-CoV-2 agent
  20. Process intensification and digital twin – the potential for the energy transition in process industries
  21. Photovoltaic properties of novel reactive azobenzoquinolines: experimental and theoretical investigations
  22. Accessing the environmental impact of tellurium metal
  23. Membrane-based processes in essential oils production
  24. Development of future-proof supply concepts for sector-coupled district heating systems based on scenario-analysis
  25. Educators’ reflections on the teaching and learning of the periodic table of elements at the upper secondary level: a case study
  26. Optimization of hydrogen supply from renewable electricity including cavern storage
  27. A short review on cancer therapeutics
  28. The role of bioprocess systems engineering in extracting chemicals and energy from microalgae
  29. The topology of crystalline matter
  30. Characterization of lignocellulosic S. persica fibre and its composites: a review
  31. Constructing a framework for selecting natural fibres as reinforcements composites based on grey relational analysis
  32. Polybutylene succinate (PBS)/natural fiber green composites: melt blending processes and tensile properties
  33. The properties of 3D printed poly (lactic acid) (PLA)/poly (butylene-adipate-terephthalate) (PBAT) blend and oil palm empty fruit bunch (EFB) reinforced PLA/PBAT composites used in fused deposition modelling (FDM) 3D printing
  34. Thermal properties of wood flour reinforced polyamide 6 biocomposites by twin screw extrusion
  35. Manufacturing defects and interfacial adhesion of Arenga Pinnata and kenaf fibre reinforced fibreglass/kevlar hybrid composite in boat construction application
  36. Wettability of keruing (Dipterocarpus spp.) wood after weathering under tropical climate
  37. Simultaneous remediation of polycyclic aromatic hydrocarbon and heavy metals in wastewater with zerovalent iron-titanium oxide nanoparticles (ZVI-TiO2)
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 10.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/psr-2021-0119/html
Scroll to top button