New methodology of heterocyclization: The electrophilic addition reactions of selenium di- and tetrahalides and tellurium tetrachloride to diethynyl silanes and germanes

Mini-Reviews in Organic Chemistry

Volumn 7, Issue 1, 2010, Pages 23-32

  Amosova, S V ^a   Martynov, A V ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

Diorganyl diethynyl germanes; Diorganyl diethynyl silanes; Selenium dihalides; Selenium tetrahalides; Tellurium tetrachloride; Unsaturated five membered heterocycles

Indexed keywords

ADDITION REACTIONS; CYCLIZATION; SELENIUM COMPOUNDS; TELLURIUM COMPOUNDS;

DIHALIDES; DIORGANYL DIETHYNYL GERMANE; DIORGANYL DIETHYNYL SILANE; ELECTROPHILIC ADDITION REACTIONS; GERMANES; GERMANIUMS (GE); HETEROCYCLIZATIONS; SELENIA DIHALIDE; SELENIA TETRAHALIDE; UNSATURATED FIVE-MEMBERED HETEROCYCLES;

SILANES;

EID: 77949605231     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (75)

1. Kirmse, W.; Horner, L. Über Lichtreaktionen VIII. Photolyse von 1.2.3-Thiodiazolen. Justus Liebigs Ann. Chem., 1958, 614, 4-18.
2. Mayer, R.; Hunger, B.; Prousa, R.; Müller, A.-K. Organische Schwefelverbindungen.81. Zur Einwirkung von Schwefelkohlenstoff und Schwefel auf Phenylacety-len. J. Prakt. Chem., 1967, 35, 294-301.
3. Lalezali, I.; Shafiee, A.; Yalpani, M. Selenium heterocycles. VI. Mechanism of the stereoselective formationof 1,4-diselenafulvenes from 1,2,3-selenadiazoles and base. J. Org. Chem.,1973, 38, 338-340.
4. Sukhai, R.S.; Veerboom, W.; Meijer, J.; Schoufs, M.J.M.; Brandsma, L. A convenient synthesis of 1,3-dithioles, 1,3-thiaselenoles and 1,3-thiatelluroles. Rec. Trav. Chim. Pays-Bas, 1981, 100,10-13.
5. Potapov, V.A.; Gusarova, N.K.; Amosova, S.V.; Kashik, A.S.; Trofimov, B.A. Reactions of chalcogens with phenylacetylene. Sulfur Lett.,1985, 4, 13-18.
6. Potapov, V.A.; Kashik, A.S.; Amosova, S.V. Phase transfer catalyzed synthesis of Z-2-benzylidene-4-phenyl-1,3-diselenole from metallic selenium and phenylacetylene. Chem. Heterocycl. Compd. 1987, 23,1035.
7. Potapov, V.A.; Amosova, S.V.; Kashik, A.S. Reactions of seleniumand tellurium metals with phenylacetylene in three-phase catalytical systems. Tetrahedron Lett., 1989, 30, 613-616.
8. Sadekov, I.D.; Minkin, V.I. Specificfeatures of the reactivity of organotellurium compounds. Russ. Chem. Revs.,1995, 64, 491-522.
9. Wang, J. X.; Zhao, K. Synthesis of cis- and trans-2,6-diphenyl-1,4-diselenafulvenes from phenylacetylene with selenium and baseunder PTC-ultrasonic conditions. Synth. Commun., 1996, 26, 1617-1622.
10. Gorgues, A.; Hudhomme, P.; Salle, M. Highly functionalized tetrathiafulvalenes: riding along the synthetic trail from electrophilic alkynes. Chem. Rev.,2004, 104, 5151-5184.
11. Lakshmikantham, M.V.; Aqad, E.; Rajagopal, D.; Cava, M.P. Aspects of organoselenium and organotellurium chemistry. Phosphorus Sulfur Silicon Relat. Elem., 2005, 180, 787-800.
12. Bryce, M. R. Functionalised tetrathiafulvalenes: new applications asversatile -electron systems in materials chemistry. J. Mater. Chem. 2000,10, 589-598.
13. Nielsen, M. B.; Lomholt, C.; Becher, J. Tetrathiafulvalenesas building blocks in supramolecular chemistry. Chem. Soc. Rev., 2000, 29,153-164.
14. Segura, J. L.; Martín, N. New concepts in tetrathiafulvalenechemistry. Angew. Chem. Int. Ed., 2001, 40, 1372-1409.
15. Becher, J.; Jeppesen, J.O.; Nielsen, K. Tetrathiafulvalenes: from heterocyclic chemistry tomolecular devices. Synth. Methods, 2003, 133-134, 309-315.
16. Jeppesen, J.O.; Becher, J. Pyrrolo-tetrathiafulvalenes and their applications in molecu-lar and supramolecular chemistry. Eur. J. Org. Chem. 2003, 3245-3266.
17. Schukat, G.; Fanghänel, E. Synthesis, reactions, and selected physico-chemical properties of 1,3- and 1,2-tetrachalcogenafulvalenes. J. SulfurChem., 2003, 24, 1-190.
18. Otsubo, T.; Takimiya, K. Recent synthetic ad-vances of tetrathiafulvalene-based organic conductors. Bull. Chem. Soc. Jpn.2004, 77, 43-58.
19. Bendikov, M.; Wudl, F.; Perepichka, D. F. Tetrathiaful-valenes, oligoacenenes, and their buckminsterfullerene derivatives: the brickand mortar of organic electronics. Chem. Rev., 2004, 104, 4891-4945.
20. Fabre, J. M. Synthesis strategies and chemistry of nonsymmetrically substi-tuted tetrachalcogenafulvalenes. Chem. Rev., 2004, 104, 5133-5150.
21. Jeppesen, J. O.; Nielsen, M. B.; Becher, J. Tetrathiafulvalene cyclophanesand cage molecules. Chem. Rev., 2004, 104, 5115-5131.
22. Tanabe, J.; Terao, H.; Matsushita, M.M.; Sugawara, T.; Kudo, T.; Tejima, T.; Izuoka, A.; Kawada, Y. Polyhedral building block with specific facial interaction for conducting supramolecular self-assembly. J. Mater. Chem., 2004, 14, 2842-2847.
23. Mori, T. Organic conductors with unusual band fillings. Chem. Rev., 2004,104, 4947-4969.
24. Yamada, J.; Akutsu, H.; Nishikawa, H.; Kikuchi, K. Newtrends in the synthesis of -electron donors for molecular conductors and su-perconductors. Chem. Rev., 2004, 104, 5057-5083.
25. Iyoda, M.; Hasegawa, M.; Miyake, Y. Bi-TTF, bis-TTF, and related TTF oligomers. Chem. Rev.,2004, 104, 5085-5113.
26. Geiser, U.; Schlueter, J.A. Conducting organic radical cation salts withorganic and organometallic anions. Chem. Rev., 2004, 104, 5203-5241.
27. Kato, R. Conducting metal dithiolene complexes: structural and electronicproperties. Chem. Rev., 2004, 104, 5319-5346.
28. Coronado, E.; Day, P. Magnetic molecular conductors. Chem. Rev., 2004, 104, 5419-5448.
29. Lorcy, D.; Bellec, N. Dithiadiazafulvalenes: promising precursors of molecular materials. Chem. Rev., 2004, 104, 5185-5202.
30. Migalina, Yu.V.; Balog, I.M.; Lendel, V.G.; Koz'min, A.S.; Zefirov, N.S. Reactions of tellurium tetrahalides with 1,5- and 1,6-diolefins and their de-rivatives. Chem. Heterocycl. Compd., 1978, 14, 976-979.
31. Migalina, Yu.V.; Staninets, V.I.; Lendel, V.G.; Balog, I.M.; Palyulin, V.A.; Koz'min, A.S.; Zefirov N.S. Organic compounds of selenium and tellurium. I. Reaction ofselenium tetrahalides with 1,5- and 1,6-diolefins and their derivatives. Chem. Heterocycl. Compd., 1977, 13, 49-53.
32. Lendel, V.G.; Sani, A.Yu.; Migalina, Yu.Yu.; Pak, B.I.; Balog I.M. Synthesis of perhydro-1,4-selenazinesand perhydro-1,4-tellurazines containing a sulfamide group. Chem. Hetero-cycl. Compd., 1989, 25, 474-476.
33. Laitalainen, T.; Sundberg, M.R.; Uggla, R.; Bergman J. Stereoselectivesynthesis, molecular structure and NBO analyses of cis-3,5-di(chloromethyl)-1,4-oxatellurane(IV) 4,4-dichloride. Polyhedron, 1997, 16,2441-2445.
34. Bergman, J.; Laitalainen, T.; Sundberg, M.R.; Uggla, R.; Kivekas R. Stereo-chemical synthesis and crystal structure of the racemate of 1-thia-2-tellura-1(1-allyl-4-chloro)cyclopentane 2,2,2-trichloride. Polyhedron, 1998, 17,2153-2159.
35. Lautenschlaeger, F. The reaction of sulfur dichloride with linear diolefins.Stereochemical aspects in the formation of cyclic sulfides. J. Org. Chem.,1968, 33, 2620-2627.
36. Tavares, P.; Meunier, P.; Kubicki, M.M.; Gautheron, B.; Dousse, G.; Lavayssiére, H.; Satgé, J. Benzodiselenagermoles and spirobisbenzodisele-nagermoles. Heteroatom. Chem., 1993, 4, 383-392.
37. Majoral, J.-P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Zir-conocene [Cp2Zr] synthon and benzynezirconocene complexes as tools inmain group element chemistry. Coord. Chem. Rev., 1998, 178-180, 145-167.
38. Block, E.; Aslam M. The chemistry of mixed organosulfur-silicon com-pounds. Tetrahedron, 1988, 44, 281-324.
39. Rousseau, G.; Blanco, L. Het-erocyclic compounds with a silicon atom and another non-adjacent different heteroatom. Tetrahedron, 2006, 62, 7951-7993.
40. Voronkov, M.G.; Kir-pichenko, S.V.; Suslova, E.N.; Keiko, V.V. The synthesis and some proper-ties of 1-thia-3-silacyclobutanes and 1-thia-3-silacyclopentane. J. Or-ganomet. Chem., 1981, 204, 13-19.
41. Voronkov, M.G.; Barton, T.J.; Kir-pichenko, S.V.; Keiko, V.V.; Pestunovich, V.A. The new heterocyclic systems 1-thia-3-silacyclobutane and 1-thia-3-silacyclopentane. Russ. ChemBull., 1976, 25, 702.
42. Voronkov, M.G.; Kirpichenko, S. V.; Keiko, V.V.; Tseitlina, E.O. Reaction of diethylsilane with dialkenyl sulfides as a path forthe synthesis of heterocyclic systems containing silicon and sulfur atoms. Russ. Chem. Bull., 1981, 30, 152-156.
43. Detty, M.R.; Murray, B.J.; Seidler, M.D. Preparation of 2,6-diphenyl-4H-chalcogenapyran-4-ones. J. Org. Chem., 1982, 47, 1968-1969.
44. Detty, M.R.; Murray, B.J.; Perlstein, J.H. Conducting salts of (telluro-pyranyl)telluropyrans. Tetrahedron Lett., 1983, 24, 539-542.
45. 4,4' -4-chalcogenapyranyl-4h-chalcogenapyrans: Synthesis, electrochemical oxidation, and esr investigations of radical-cation states. Tetrahedron, 1985, 41, 4853-4859.
46. Wad-sworth, D.H.; Geer, S.V.; Detty, M.R. Preparation of arylpropiolate estersfrom trichlorocyclopropenium cation and elaboration of the esters to un-symmetrical 1,4-pentadiyn-3-ones and unsymmetrical tellurapyranones. J.Org. Chem., 1987, 52, 3662-3668.
47. Detty, M.R.; Luss, H.R. Addition ofdisodium chalcogenides to 1,5-bis(trimethylsilyl)penta-1,4-diyn-3-one. Syn-theses, structure, and reactivity of the parent Δ -4H-chalcogenapyran-4-ones. Organometallics, 1992, 11, 2157-2162.
48. Meijer, J.; Vermeer, P.; Verkrujsse H.D.; Brandsma, L. Chemistry of acety-lenic ethers 102. Reaction of di(1-alkynyl) sulfides with sodium sulfide, selenide and telluride. Formation of 1,4-dithiins, 1,4-thiaselenins and 1,4-thiatellurins. Rec. Trav. Chim. Pays-Bas, 1973, 92, 1326-1330.
49. Potapov, V.A.; Amosova, S.V.; Belozerova, O.B.; Albanov, A.I.; Yarosh, O.G.; Voronkov, M.G. Synthesis of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes. Chem. Heterocycl. Compd., 2003, 39, 549-550.
50. Potapov, V.A.; Amosova, S.V. New methods for preparation of organoseleniumand organotellurium compounds from elemental chalcogens. Russ. J. Org.Chem., 2003, 39, 1373-1380.
51. Amosova, S.V.; Martynov, A.V.; Mahaeva, N.A.; Belozerova, O.A.; Penzik, M.V.; Albanov, A.I.; Yarosh, O. G.; Voronkov, M. G. Unsaturated five-membered selenium-silicon containing heterocycles based on the reactions of selenium di- and tetrahalides with dior-ganyl diethynyl silanes. J. Organomet. Chem., 2007, 692, 946-952.
52. Amosova, S.V.; Penzik, M.V.; Martynov, A.V.; Makhaeva, N.A.; Yarosh, N.O.; Voronkov, M.G. Unsaturated five-membered selenium-germaniumcontaining heterocycles based on the reactions of selenium di- and tetrahalides with diorganyl diethynyl germanes. J. Organomet. Chem., 2008, 693,3346-3350.
53. Amosova, S.V.; Penzik, M.V.; Albanov, A.I.; Potapov, V.A. Addition of selenium dibromide to divinyl sulfide: spontaneous rearrangement of 2,6-dibromo-1,4-thiaselenane to 5-bromo-2-bromomethyl-1,3-thiaselenolane. Tetrahedron Lett., 2009, 50, 306-308.
54. Potapov, V.A.; Volkova, K.A.; Penzik, M.V.; Albanov, A.I.; Amosova, S.V. Reaction of selenium dichloridewith divinyl selenide. Russ. J. Org. Chem., 2008, 44, 1556-1557.
55. Potapov, V.A.; Kurkutov, E.O.; Albanov, A.I.; Amosova, S.V. Regio- and stereo selective addition of selenium dibromide to divinyl sulfone. Russ. J. Org. Chem.,2008, 44, 1547-1548.
56. Amosova, S.V.; Abramova, E.V.; Potapov, V.A. Selenium dibromide as a mild brominating agent. Russ. J. Gen. Chem., 2008,78, 1463.
57. Amosova, S.V.; Penzik, M.V.; Albanov, A.I.; Potapov, V.A. Reaction of selenium dibromide with divinyl sulfide. Russ. J. Gen. Chem.,2009, 79, 161.
58. Milne, J. Selenium dibromide and dichloride in acetonitrile. Polyhedron,1985, 4, 65-68.
59. 77Se NMR study. Polyhedron, 1990, 9, 589-595.
60. Maaninen, A.; Chivers, T.; Parvez, M.; Pietikalinen, J.; Laitinen, R.S. Syntheses of THF solutions of SeX2 (X = Cl, Br) and a new route to seleniumsulfides SenS8-n (n = 1-5): X-ray crystal structures of SeCl2(tht)2 andSeCl2.tmtu. Inorg. Chem., 1999, 38, 4093-4097.
61. Martynov, A.V.; Makhaeva, N.A.; Amosova, S.V. Reaction of dimethyldi-ethynylsilane with 1,2-dichlorodiselane. Russ. J. Gen. Chem., 2009, 79, 334-335.
62. Potapov, V.A.; Amosova, S.V.; Belozerova, O.B.; Albanov, A.I.; Yarosh, O.G.; Voronkov, M.G. Reaction of selenium tetrabromide with dimethyldi-ethynylsilane. Chem. Heterocycl. Compd., 2003, 39, 551-552.
63. Amosova, S.V.; Shagun, V.A.; Martynov, A.V.; Makhaeva, N.A.; Larina, L.I.; Lysenko, K.A.; Voronkov, M.G. Mechanism of the cyclization of di-methyl diethynyl silane with selenium tetrabromide: computational andstructural studies, and monitoring. J. Organomet. Chem., 2007, 692, 3307-3315.
64. Amosova, S.V.; Martynov, A.V.; Penzik, M.V.; Makhaeva, N.A.; Potapov, V.A.; Albanov, A.I.; Zhilitskaya, L.V.; Voronkov, M.G. 4,4-Diorganyl-1,1,3,6-tetrachloro-1,4-tellura(IV)silafulvenes - new class of tellurium-silicon containing heterocycles. J. Organomet. Chem., 2008, 693, 3650-3654.
65. Amosova, S.V.; Penzik, M.V.; Martynov, A.V.; Zhilitskaya, L.V.; Vo-ronkov, M.G. Electrophilic addition of selenium and tellurium halides tomethyldiethynylsilane. Russ. J. Gen. Chem., 2009, 79, 221-227.
66. Amosova, S.V.; Martynov, A.V.; Shagun, V.A.; Musalov, M.V.; Larina, L.I.; Krivdin, L.B.; Zhilitskaya, L.V.; Voronkov, M.G. Anti-Markovnikovaddition of tellurium tetrachloride to trimethyl ethynyl silane. J. Organomet.Chem., 2008, 693, 2509-2513.
67. Martynov, A.V.; Amosova, S.V. First example of the anti-Markownikoff addition of tellurium tetrachloride to terminal acetylene, trimethyl ethynyl silane. Russ. J. Gen. Chem., 2008, 78, 2067-2070.
68. 3JSe-Se coupling allowingcis/trans isomer assignments in substituted tetraselenafulvalenes. J. Am.Chem. Soc., 1984, 106, 1240-1243.
69. 29Si Nuclear Magnetic Resonance in Determination of Organic Structure by Physical Methods; Nachod, F.C.; Zuckermann, J.J.; Randall, E.W., Eds.; Academic Press: New York, 1976; p. 254.
70. 77Se NMR. 2. The Basis for application of JSe-Se and JSe-H in structure assignments of mono-, di-, and triseleno-substituted alkenes. J. Org. Chem., 1986, 51, 1657-1663.
71. 1H spin-spin coupling constants. Magn. Reson. Chem., 2008, 46, 979.
72. Luthra, N.D.; Odom, J.D. The Chemistry of Organic Selenium and Tellurium Compounds: Nuclear Magnetic Resonance and Electron Spin Resonance Studies of Organic Selenium and Tellurium Compounds; Rappoport, Z.; Patai S., Eds.; John Wiley and Son Ltd: New York, 1986; Vol. 1, p. 189.
73. 125Te} Heteronuclear mag-netic double resonance in some organotellurium compounds. J. Organomet.Chem., 1976, 113, 139-141.
74. 125Te-NMR-spektren von organotellurhalogeniden. J. Organomet. Chem., 1982, 232,147-150.
75. Klyba, L.V.; Amosova, S.V.; Belozerova, O.B.; Potapov, V.A.; Zhan-chipova, E.R.; Yarosh, O.G.; Voronkov, M.G. Mass spectra of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes and 2,4-dihalo-2-dihalomethyl-3,3-dimethyl-1-selena-3-silacyclopent-4-enes. Russ. Chem. Bull., 2005, 54, 650-653.