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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Published in | Tetrahedron Vol. 50; no. 29; pp. 8765 - 8772 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Elsevier Ltd
1994
Elsevier |
Subjects | |
Online Access | Get full text |
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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.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/S0040-4020(01)85350-3 |