Formation of Tetrahydrofuran Derivatives and Acetonylation of Alkenes Using Carbon Radicals Derived from Manganese(III) Oxidation of Diketene.
J Org Chem
; 61(23): 8264-8271, 1996 Nov 15.
Article
em En
| MEDLINE
| ID: mdl-11667814
ABSTRACT
Oxidation of a mixture of diketene and a 1,1-diarylethene 1 with manganese(III) acetate dihydrate gave an equilibrium mixture of 5-hydroxy-2-pentanone 2 and a tetrahydrofuran-2-ol, which was subsequently dehydrated in glacial acetic acid to yield 4-penten-2-one 4 in good yield. A similar reaction in the presence of alcohols or amines afforded 2-alkoxy-2-methyltetrahydrofurans 5 or 3-acetyl-2-aminodihydrofurans 9 in moderate yields. Diketene reacted with manganese(III) acetate in the presence of nucleophiles, such as water and alcohols, to give a mixture of unconjugated manganese(III) enolate A and conjugated manganese(III) enolate B. Major products 4 and 5 were formed by the oxidation of the conjugated manganese(III) enolate B. Tetrahydrofurylideneacetates 3 and 7 derived from the unstable unconjugated enolate A were also obtained as minor products. The reaction pathways are discussed.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
1996
Tipo de documento:
Article