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Volumn , Issue 17, 2007, Pages 2663-2666

Regio- and stereospecific synthesis of functionalized divinyl selenides

Author keywords

Alkynes; Divinyl diselenides; Divinyl selenides; Electrophilic addition; Regioselectivity; Selenium; Stereoselectivity

Indexed keywords

1 HYDROXYMETHYL 2 CHLOROVINYL SELENIDE; SELENIDE; UNCLASSIFIED DRUG;

EID: 35748986158     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991051     Document Type: Article
Times cited : (22)

References (35)
  • 14
    • 35748935416 scopus 로고    scopus 로고
    • Representative Procedure for the Preparation of (3Z, 4-Chloro-3, Z)-2-chloro-1-(1-hydroxy-1-methylethyl)vinyl]selanyl, 2-methylbut-3-en-2-ol (1e) The THF solution of selenium dichloride (1 mmol) prepared by the known procedure3 was added dropwise to a solution of 2-methylbut-3-yn-2-ol (172 mg, 2 mmol) in dry THF (2 mL) at 0°C. Then the reaction mixture was stirred at r.t. for 35 min. After completion of the reaction (TLC, the reaction mixture was extracted with EtOAc (20 mL) and washed with H2O (5 mL) and brine (2 x 5 mL, The organic layer was dried over Mg2SO4. After evaporation of the solvent the crude product, containing 92% of selenide 1e and 8% of diselenide 2e, was obtained. After column chromatography with silica gel (hexanes-EtOAc, 4:1) pure 1e was obtained 264 mg, 82% yield
    • 4. After evaporation of the solvent the crude product, containing 92% of selenide 1e and 8% of diselenide 2e, was obtained. After column chromatography with silica gel (hexanes-EtOAc, 4:1) pure 1e was obtained (264 mg, 82% yield).
  • 15
    • 35748986297 scopus 로고    scopus 로고
    • Analytical and Spectroscopic Data for Representative Compounds (2Z)-3-Chloro-2, Z)-2-chloro-1-(hydroxymethyl) vinyl]selanyl}prop-2-en-1-ol (1a) Viscous liquid. IR (neat, 3453 (br, 2972, 1571, 1368, 1169, 1129, 980 cm-1. 1H NMR (600 MHz, CDCl3, δ, 3.62 (br s, 2 H, OH, 4.46 (d, 4 H, J, 1.1 Hz, 6.55 (t, 2 H, J, 1.1 Hz, 13C NMR (150 MHz, δ, 60.9 (CH2, 122.2 (CH, 2JC,Se, 22.6 Hz, 132.8 (C, 1JC,Se, 112.6 Hz, HRMS: m/z calcd for C6H8Cl2O278Se: 259.9074; found: 259. 9058, 2Z)-3-Chloro-2, 1 Z)-2-chloro-1-(hydroxy methyl)prop-1-enyl]selanyl}but-2-en-1-ol (1b) Solid, mp 56-58°C. IR (KBr, 3324 (br, 2976, 1606, 1455. 1015 cm-1. 1H NMR 600 MHz, CDCl3, δ, 2.4
    • C,Se = 15.9 Hz).
  • 22
    • 0001884533 scopus 로고    scopus 로고
    • Organoselenium Chemistry. Modern Developments in Organic Synthesis
    • For recent reviews, see: a, Wirth, T, Ed, Springer: Berlin
    • For recent reviews, see: (a) Tiecco, M. Organoselenium Chemistry. Modern Developments in Organic Synthesis, In Topics in Current Chemistry, Vol. 208; Wirth, T., Ed.; Springer: Berlin, 2000, 7.
    • (2000) Topics in Current Chemistry , vol.208 , pp. 7
    • Tiecco, M.1
  • 24
    • 0004112604 scopus 로고    scopus 로고
    • Back, T. G, Ed, Oxford University Press: Oxford UK
    • (c) Beaulieu, P. L.; Deziel, R. In Organoselenium Chemistry; Back, T. G., Ed.; Oxford University Press: Oxford UK, 1999, 35.
    • (1999) Organoselenium Chemistry , pp. 35
    • Beaulieu, P.L.1    Deziel, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.