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Phthalides and 1,3-indandiones. XXVI. Perkin synthesis of the cis and trans isomers of 3-(α-naphthyloxymethylene)phthalide and their rearrangements to 1,3-indandiones

M. Furdík, M. Lacová, M. Livař, and J. Hrivňák

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, Komenský University, Bratislava


Abstract: So far not reported cis- and trans-isomeres of 3-(α-naphtoxy-methylene)phtalide and its ß-naphtoxy analog were synthetised by the Gabriel modification of Perkin synthesis, starting from the corresponding naphtoxyacetic acids. So as it was proved with 3-phenoxy-methylenephtalide[l],the cis-derivatives of the mentioned compounds could exist under the conditions of the reaction in question. By the sodium msthoxide catalysed rearrangement, 2-(α-naphtoxy)-indane-1,3-dione and its ß-analog were obtained. The infra-red absorption spectra proved the identity of cis- and trans-isomeres of the respective phtalides. The analysis of the results obtained from gas-chrom apograph у explained the relatively higher polarity of trans-isomeres of the studied phtalides, comparing with their cis- isomeres, and consequently the electrone-pushing effect of phenoxy and naphtoxy groups. The chromatogram also showed, that ß-naphtoxy group increases more the polarity of phtalide molecule as did α-naphtoxy group.

Full paper in Portable Document Format: 2011a834.pdf (in Slovak)


Chemical Papers 20 (11) 834–842 (1966)

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