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Volumn , Issue 4, 1999, Pages 486-488

A new method for the synthesis of normal and medium ring silylated unsaturated thiolactones

Author keywords

(Z) carboxy silyl Enethiols; Polyphosphate esters; Thiolactones; Carboxy acylsilanes

Indexed keywords

SUCCINIC ACID; THIOLACTONE;

EID: 0032947473     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-6182     Document Type: Article
Times cited : (8)

References (31)
  • 18
    • 0344366776 scopus 로고    scopus 로고
    • note
    • f fraction the co-carboxy acylsilane 1 as a yellow oil.
  • 21
    • 0345229533 scopus 로고    scopus 로고
    • note
    • General procedure for the preparation of 2: hydrogen chloride and hydrogen sulfide were bubbled into a solution of the CD-carboxy acylsilane 1 (1.0 mmol) in anhydrous diethyl ether (50 mL) at-20°C, until the starting acylsilane had disappeared (TLC with 1:1 light petroleum-diethyl ether as eluent). The mixture was allowed to warm to room temperature and solid sodium hydrogen carbonate was added to the solution until the evolution of carbon dioxide ceased (10 g), then the reaction was left overnight. The crude, filtered and concentrated under reduced pressure, gave the (Z)-ω-carboxy-α-silyl enethiol 2 in a pure form.
  • 22
    • 0344366771 scopus 로고    scopus 로고
    • note
    • 2Ph). Irradiation of the dimethylsilyl signal at 0.62 ppm produced a significant increase (15%) of the intensity of the signal of the vinylic proton at 6.18 ppm.
  • 24
    • 0344366774 scopus 로고    scopus 로고
    • note
    • 3 (8 mL) was stirred at room temperature for 12h or at 40°C for 2h. The reaction mixture was treated with saturated aqueous ammonium chloride and extracted with chloroform. The organic layer was dried with sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (light petroleum-ethyl acetate 10:1 as eluent) gave the title product as a yellow oil.
  • 25
    • 0344366773 scopus 로고    scopus 로고
    • note
    • 2Ph).
  • 26
    • 0344366772 scopus 로고    scopus 로고
    • note
    • 2Ph).
  • 28
    • 0344366770 scopus 로고    scopus 로고
    • note
    • 3, but the reactions failed and we isolated only undesired products among which were the ethyl esters of 2d and 2e.
  • 29
    • 0344798537 scopus 로고    scopus 로고
    • note
    • 2Ph).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.