Naslov
Synthesis of asymmetrically disubstituted anthracenes

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

Izvornik
Tetrahedron (0040-4020) 73 (2017), 40; 5892-5899

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA