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izvor podataka: crosbi

Synthesis of asymmetrically disubstituted anthracenes (CROSBI ID 241511)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Škalamera, Đani ; Veljković, Jelena ; Ptiček, Lucija ; Sambol, Matija ; Mlinarić-Majerski, Kata ; Basarić, Nikola Synthesis of asymmetrically disubstituted anthracenes // Tetrahedron, 73 (2017), 40; 5892-5899. doi: 10.1016/j.tet.2017.08.038

Podaci o odgovornosti

Škalamera, Đani ; Veljković, Jelena ; Ptiček, Lucija ; Sambol, Matija ; Mlinarić-Majerski, Kata ; Basarić, Nikola

engleski

Synthesis of asymmetrically disubstituted anthracenes

We have developed synthetic pathways toward differently substituted hydroxyanthracenes (anthrols) with the aim to investigate their photochemical reactivity in dehydration reactions. Although the syntheses of anthracenes substituted at positions 9, 10 are well known, reports for the synthesis of anthracenes with different substitution patterns are scarce. Herein we review known and report novel synthetic pathways toward anthrols with substituents at 1, 2-, 2, 3- and 2, 6- positions. We present two synthetic approaches: (i) building of the anthracene tricyclic fused ring system from the appropriate benzene derivatives, and (ii) reduction of the corresponding anthraquinones. Reduction of 2-hydroxyanthracene-1-carbaldehyde to the corresponding alcohol yields rather unexpected 1, 1'-methylenedianthracen-2-ol, whose proposed mechanism of formation is supported by experimental observations and calculations.

anthracene ; 1-anthrol ; 2-anthrol ; dehydroxymethylation ; anthracene carbaldehyde

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Podaci o izdanju

73 (40)

2017.

5892-5899

objavljeno

0040-4020

10.1016/j.tet.2017.08.038

Povezanost rada

Kemija

Poveznice
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