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Volumn 45, Issue 11, 2004, Pages 2367-2370

Rhodium(I)-catalyzed regioselective additions of chloroformates to 1,2-dienes

Author keywords

Addition; Allene; Chloroformate; Rhodium

Indexed keywords

ALKADIENE; ALLENE DERIVATIVE; ESTER DERIVATIVE; FORMIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM;

EID: 1242286935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.102     Document Type: Article
Times cited : (17)

References (27)
  • 21
    • 85030908929 scopus 로고    scopus 로고
    • note
    • General procedure for rhodium-catalyzed additions of chloroformate esters to allenes. In a thick-walled Pyrex tube was placed a mixture of an allene (0.5 mmol), compound 2 (2.5 mmol), rhodium catalyst (0.025 mmol) and toluene (1.0 mL) under nitrogen. The tube was then flame-sealed and the mixture was heated at 110°C for 20 h with stirring. After cooling, the reaction mixture was diluted with toluene to 2.0 mL and was analyzed by gas chromatography after addition of an appropriate amount of eicosane as internal standard. Volatiles were removed in vacuo and the residue was purified by column chromatograph (silica gel, eluted with hexane) and further by preparative TLC (silica gel, eluted with a 6:1 hexane-diethyl ether mixture) to afford 3 as colorless oil.
  • 22
    • 85030893821 scopus 로고    scopus 로고
    • note
    • All products 3 were isolated and gave satisfactory spectral and/or analytical data reported below.
  • 23
    • 85030912869 scopus 로고    scopus 로고
    • note
    • br., 1H).
  • 24
    • 85030912544 scopus 로고    scopus 로고
    • note
    • GC-MS analysis of the reaction mixture disclosed that the reaction produced three adducts in a ratio of 12:61 ( 3g ):27. The structures of the two minor isomers have not been characterized yet.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.