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

Tetrahedron Letters

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

  Hua, Ruimao ^a   Tanaka, Masato ^b,c  

^a TSINGHUA UNIVERSITY   (China)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c Tokyo Institute of Technology ^*  (Japan)

Author keywords

Addition; Allene; Chloroformate; Rhodium

Indexed keywords

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

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; REACTION ANALYSIS;

EID: 1242286935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.102     Document Type: Article

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21. 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. All products 3 were isolated and gave satisfactory spectral and/or analytical data reported below.
23. br., 1H).
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