- Synthesis of formyl derivatives of benzocrown ethers containing N, S, and O heteroatoms in the macrocycle
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A method for the synthesis of 4'-bromobenzodithia-15(18)-crown-5(6) and 4'-bromobenzodiaza-15(18)-crown-5(6) by condensation of 3,4-di(2'-haloethoxy)bromobenzene with polyoxaalkanes containing terminal SH or NHMe groups was suggested.The method for the synthesis of formyl derivatives of benzocrowns containing N, S, and O heteroatoms in the macrocycle based on the metallation of appropriate bromo derivatives with BunLi followed by treatment of the resulting organolithium intermediates with DMF was developed.Oximes and semicarbazones of benzaldehydes containing a crown ether fragment were obtained, and their transformation into the original aldehydes by treatment with KNO2 in an acid medium was studied. - Key words: 4'-bromobenzocrowns, synthesis, metallation; 4'-formylbenzocrown ethers; semicarbazones and oximes of 4'-formylbenzocrown ethers.
- Gromov, S. P.,Fedorova, O. A.,Vedernikov, A. I.,Samoshin, V. V.,Zefirov, N. S.,Alfimov, M. V.
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p. 116 - 123
(2007/10/02)
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- The Photochemistry of the Host-Guest Complex. V. The Effect of the Sodium Ion on the Photoreaction of Benzil Derivatives with a Crown Ether Moiety
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The photolysis of 4'-(2-phenyl-1,2-dioxoethyl)benzo-15-crown-5 in benzene containing 1-dodecanethiol gives benzaldehyde and 4'-formylbenzo-15-crown-5.The formation of the aldehydes was inhibited by the sodium ion, whereas the photolysys of 1-(3,4-dimethoxyphenyl)-2-phenylethanedione was not inhibited by the sodium ion.This inhibition must be due to the decrease in the formation of benzoyl radicals from the triplet excited state of the crown ether derivative.The salt effect was discussed on the basis of the spectral data.
- Hirano, Hideki,Kurumaya, Katsuyuki,Tada, Masaru
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p. 2708 - 2711
(2007/10/02)
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