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- Title
Unexpected Products from the Reaction of 2,2,4,4- Tetramethylcyclobutane-1,3-dione with the Ma˛kosza Reagent.
- Authors
Mlostoń, Grzegorz; Romański, Jaroslaw; Linden, Anthony; Heimgartner, Heinz
- Abstract
Reaction of 2,2,4,4-tetramethylcyclobutane-1,3-dione ( 2) under phase-transfer-catalysis (PTC) conditions (CHCl3/aqueous NaOH) yielded a complex mixture of unexpected products ( Scheme 2). From the organic phase, three ring-enlarged products 7 - 9 with a cyclopentane-1,3-dione ( cf. 7 and 9) or a cyclopentenone skeleton ( cf. 8) were isolated in low yield. After acidification of the aqueous phase, the oily residue was treated with CH2N2, and methyl 3-oxopentanoate 12 and dimethyl 2-hydroxybutanedioate 13 were obtained in almost equal amounts. The structures of 8 and 9 were established by X-ray crystal-structure analysis ( Fig.). Mechanisms for the formation of the products, initiated by nucleophilic attack of trichloromethanide ion and opening of the cyclobutane ring, are proposed in Schemes 3 and 4.
- Publication
Helvetica Chimica Acta, 1999, Vol 82, Issue 8, p1302
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/(SICI)1522-2675(19990804)82:8<1302::AID-HLCA1302>3.0.CO;2-A