Template effect in the synthesis of formyl derivatives of benzothiacrown compounds |
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| Authors: | O A Fedorova A I Vedernikov O V Yescheulova P V Tsapenko Yu V Pershina S P Gromov |
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| Institution: | (1) Photochemistry Center of the Russian Academy of Sciences, 7a ul. Novatorov, 117421 Moscow, Russian Federation |
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| Abstract: | The condensation of 3,4-bis(2-haloethoxy)benzaldehydes with acyclic α,ω-alkanedithiols in the presence of alkali metal carbonates
in dry ethanol, DMF, MeCN and their mixtures with water gives formyl derivatives of benzothiacrown compounds in high yields.
The best results are attained when the radius of the hydrated metal cation fits to the crown ether cavity. In the case of
Cs+, high yields were observed for crown ethers of any size and composition; this can be explained by a specific template effect
of this cation. The influence of the nature of the leaving group in 3,4-bis(2-haloethoxy)benzaldehydes was established for
reactions with dithiols containing no ether oxygen atoms.
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya No. 11, pp. 1881–1886, November, 2000. |
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| Keywords: | 3 4-bis(2-haloethoxy)benzaldehydes α ω -alkanedithiols alkali metal carbonates template effect formyl derivatives of benzothiacrown compounds |
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