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- Title
Zur Reaktionsweise von Diphenylcyclopropenon mit β-Carbonyl-enolaten. I. Einsatz von Acetylaceton, Acetessigsäure-methylester, 2-Äthoxycarbonyl-cyclododecanon und Malonsäure-dimethylester.
- Authors
Veprek-Bilinski, Vanda; Narasimhan, Krishna; Dreiding, André S.
- Abstract
Reaction of Diphenylcyclopropenone with β-Carbonyl-enolates. I. Use of Acetylacetone, Methyl Acetoacetate, 2-Ethoxycarbonyl-cyclododecanone and Dimethyl Malonate The reaction of the sodium salts of acetylacetone ( 6), methyl acetoacetate (7), 2-ethoxycarbonyl-cyclododecanone (8), dimethyl malonate (19) and its methyl derivative 20 with diphenylcyclopropenone ( 5) in dimethylformamide at room temperature led to the unsaturated γ-lactones 14, 15, 17, 22 and 36. In the case of dimethyl malonate ( 19), the halfester 21, the acyl-malonic ester 24 and the indenone-malonic ester 23 were also isolated. Several intermediates and the final products were characterised by reactions and spectroscopically. A general mechanism is discussed for the addition of cyclo-propenones ( 1) to the enolate salts of β-dicarbonyl compounds 4 involving the bicyclic lactone-enolates 18 and 32 as intermediates. The products formed via 18 and 32 are considered to be the result of an attack of one of the oxygen atoms of the β-carbonyl-enolate anion ( 4), the product 24, on the other hand, of the attack of the α-carbon atom of 4; in both cases the attack is on the carbonyl C-atom of 5.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 8, p3018
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610827