Isomerisation of 1-methylene-2-methyl-2-(2-oxopropyl)-cyclohexanes to 2-methylene-1-methyl-1-(2-oxopropyl)-cyclohexanes by ene and retro-ene reaction

Thermal activation of the normal Claisen products, the enones 4, 7 and 14 in the presence of a catalytic amount of propionic acid generated the isomeric enones 6, 9 and 15 via the sequential intramolecular ene-reaction of the enol tautomer followed by 1,5-hydrogen transfer (or retro ene-reaction) of...

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Bibliographic Details
Published inTetrahedron Vol. 50; no. 29; pp. 8765 - 8772
Main Authors Srikrishna, Adusumilli, Venkateswarlu, Somepalli, Nagaraju, Sankuratri, Krishnan, Kathiresan
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 1994
Elsevier
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Hydrolysis
Intramolecular reaction
Acetal
Ene reaction
Isomerization
Propionic acid
Reverse reaction
Acid catalysis
Ketone
Monocyclic compound
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Summary:Thermal activation of the normal Claisen products, the enones 4, 7 and 14 in the presence of a catalytic amount of propionic acid generated the isomeric enones 6, 9 and 15 via the sequential intramolecular ene-reaction of the enol tautomer followed by 1,5-hydrogen transfer (or retro ene-reaction) of the resultant acetyl cyclopropane intermediate. Conversion of the enones 9 and 15 into the corresponding cyclohexenones 10 and 16 established the structures of the rearrangement products. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)85350-3