ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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)
Wednesday, August 10, 2022