Palladium-catalyzed intramolecular 1,2-oxidation of allenes

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3601-3604

  Jonasson, Catrin ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; CYCLIZATION; METAL BINDING; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032554996     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00559-0     Document Type: Article

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45. 4) and concentrated. The residue was purified by flash chromatography (2:1 pentane/ether) to afford the cyclized product. Method B: The same procedure as for method A but with 6-10 equiv. of LiBr, 5-6 equiv. of LiOAc, and 5-6 equiv. of BQ in 0.55M acetic acid (towards p-benzoquinone).
46. 3) δ 176.5, 137.4, 120.3,77.5, 28.4, 26.9, 25.8, 20.9.
47. This rules out an alternative mechanism of the 1,2-oxidation via an oxypalladation to give a vinylpalladium species followed by reductive elimination to form the vinyl bromide bond.