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Volumn 51, Issue 40, 2010, Pages 5258-5261

Reactions of selenium dichloride and dibromide with divinyl sulfone: Synthesis of novel four- and five-membered selenium heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

2,4 BIS(HALOMETHYL) 1,3 THIASELENETANE 1,1 DIONE DERIVATIVE; 2,6 DIHALO 1,4 THIASELENANE DERIVATIVE; 5 HALO 2 HALOMETHYL 1,3 THIASELENOLANE DERIVATIVE; 5 HALO 2 HALOMETHYL METHYLENE 1,3 THIASELENOLANE 1,1 DIONE DERIVATIVE; DIVINYL SULFONE; HETEROCYCLIC COMPOUND; PYRIDINE; SELENIUM DERIVATIVE; SELENIUM DIBROMIDE; SELENIUM DICHLORIDE; SILICA GEL; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77956342340     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.133     Document Type: Article
Times cited : (41)

References (76)
  • 57
    • 77956340789 scopus 로고    scopus 로고
    • note
    • 2SSe: C, 17.93; H, 2.26; Cl, 26.46. Found: C, 17.69;, 2.21; Cl, 26.30.
  • 58
    • 77956339858 scopus 로고    scopus 로고
    • note
    • 2SSe: C, 17.93; H, 2.26; Cl, 26.46. Found: C, 17.87;, 2.16; Cl, 26.65.
  • 59
    • 77956340977 scopus 로고    scopus 로고
    • CCDC contains the supplementary crystallographic data for the cis-diastereomer of compound 5 (CCDC 775446). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC contains the supplementary crystallographic data for the cis-diastereomer of compound 5 (CCDC 775446). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
  • 60
    • 77956338361 scopus 로고    scopus 로고
    • note
    • Typical procedure for the synthesis of compounds 5, 6, and 12. A solution of selenium dichloride was prepared by stirring a mixture of selenium (1.6 g, 20 mmol) and sulfuryl chloride (2.7 g, 20 mmol) in MeCN (15 ml) at room temperature. To the solution of selenium dichloride was added dropwise a solution of divinyl sulfone (2.36 g, 20 mmol) in MeCN (10 ml) over 5 min with stirring. The mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo at room temperature. According to NMR data, the residue (4.29 g) contained 10% (0.43 g, 82% conversion) of divinyl sulfone, 49% (2.12 g, 55% yield) of thiaselenetane 5, and 41% (1.74 g, 45% yield) of thiaselenolane 6. Column chromatography of the residue on silica gel (benzene/hexane 3:1) gave thiaselenetane 5 (1.92 g, 50% yield), thiaselenolane 6, (0.89 g, 23% yield), and thiaselenolane 12 (0.62 g, 80% yield based on consumed thiaselenolane 6).
  • 61
    • 77956341118 scopus 로고    scopus 로고
    • note
    • 2SSe: C, 13.46; H, 1.69; Br, 44.77. Found: C, 13.21; H, 1.82; Br, 44.89.
  • 62
    • 77956340402 scopus 로고    scopus 로고
    • note
    • 2SSe: C, 13.46; H, 1.69; Br, 44.77. Found: C, 13.28; H, 1.75; Br, 44.37. The amount of the minor diastereomer of thiaselenetane 8 was too low to permit the spectral characteristics to be determined.
  • 63
    • 77956340014 scopus 로고    scopus 로고
    • note
    • Typical procedure for the synthesis of compounds 7, 8, and 13. A solution of selenium dibromide was prepared by stirring a mixture of selenium (1.6 g, 20 mmol) and bromine (3.2 g, 20 mmol) in MeCN (40 ml) at room temperature. To the solution of selenium dibromide was added dropwise a solution of divinyl sulfone (2.36 g, 20 mmol) in MeCN (20 ml) over 1 h with stirring. The mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo at room temperature. According to NMR data, the residue (6.19 g) contained 8% (0.49 g, 79% conversion) of divinyl sulfone, 72% (4.47 g, 78% yield) of thiaselenetane 7, and 20% (1.24 g, 22% yield) of thiaselenolane 8. Column chromatography of the residue on silica gel (benzene/hexane 3:1) gave thiaselenetane 7 (2.40 g, 42% yield), thiaselenolane 8 (0.57 g, 10% yield), and thiaselenolane 13 (0.33 g, 62% yield based on consumed thiaselenolane 8).
  • 64
    • 77956339064 scopus 로고    scopus 로고
    • 8 we carried out the addition of selenium dichloride to phenyl vinyl sulfide leading to the Markovnikov product, bis(2-chloro-2-phenylsulfanylethyl) selenide. These results will be published elsewhere
    • 8 we carried out the addition of selenium dichloride to phenyl vinyl sulfide leading to the Markovnikov product, bis(2-chloro-2-phenylsulfanylethyl) selenide. These results will be published elsewhere.
  • 65
    • 77956345229 scopus 로고    scopus 로고
    • note
    • 2ClSSe: C, 20.75; H, 2.18; Cl, 15.31. Found: C, 20.98; H, 2.37; Cl, 15.07.
  • 66
    • 77956345026 scopus 로고    scopus 로고
    • note
    • 2BrSSe: C, 17.41; H, 1.83; Br, 28.95. Found: C, 17.21; H, 1.97; Br, 28.87.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.