ISOMERIZATION OF 1-METHYLENE-2-METHYL-2-(2-OXOPROPYL)-CYCLOHEXANES TO2-METHYLENE-1-METHYL-1-(2-OXOPROPYL)CYCLOHEXANES BY ENE AND RETRO-ENEREACTION

Authors
SRIKRISHNA A VENKATESWARLU S NAGARAJU S KRISHNAN K
Citation
A. Srikrishna et al., ISOMERIZATION OF 1-METHYLENE-2-METHYL-2-(2-OXOPROPYL)-CYCLOHEXANES TO2-METHYLENE-1-METHYL-1-(2-OXOPROPYL)CYCLOHEXANES BY ENE AND RETRO-ENEREACTION, Tetrahedron, 50(29), 1994, pp. 8765-8772
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8765 - 8772
Database
ISI
SICI code
0040-4020(1994)50:29<8765:IO1T>2.0.ZU;2-C
Abstract
Thermal activation of the normal Claisen products, the enones 4 7 and 14 in the presence of a catalytic amount of propionic acid generated t he isomeric enones 6 9 and 15 via the sequential intramolecular ene-re action of the enol tautomer followed by 1,5-hydrogen transfer (or retr o ene-reaction) of the resultant acetyl cyclopropane intermediate. con version of the enones 9 and 15 into the corresponding cyclohexenones 1 0 and 16 established the structures of the rearrangement products.