The ~, ~x'-annelation of the enamine of 1,3-dihydro-2-phenalenone with methyl ct-(bromomethyl)acrylate affords an aromatic bieyclie framework, methyl 8,9,10,1 l-telrahydro-7,11-methano-12-keto-TH-cycloocta(de)naphthalene-9-endo-carboxylate having the ester function positioned over the aromatic ring.
✦ LIBER ✦
Preferred conformations of 9-oxo-8,9,10,11-tetrahydro- and 9-hydroxy-10,11-dihydro-7h-cycloocta[de]naphthalene-8,10-dicarboxylic esters: unusually stable tautomers of β-ketoesters
✍ Scribed by Toshihiro Kamada; Osamu Yamamoto
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 245 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
It is well known that S-ketoesters assume both ketonic and enolic structures by tautomerization and such keto-enol equilibria have hitherto been observed in a number of cyclic and acyclic enolizable 8-ketoesters. 1 However, most compounds reported so far exist only as an equilibrium mixture of the keto and enol form, 1
or assume only either form of the two isomers. 2,3 As yet, such a case is not
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## Abstract A Hofmann—Martius rearrangement mechanism is suggested for the reaction of known azomethines (I) with cyclohexane‐1,3‐dione.