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4283628 
Journal Article 
Synthesis of asymmetrically disubstituted anthracenes 
Skalamera, D; Veljkovic, J; Pticek, L; Sambol, M; Mlinaric-Majerski, K; Basaric, N 
2017 
1 
Tetrahedron
ISSN: 0040-4020 
73 
40 
5892-5899 
WOS:000412036700010 
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. (C) 2017 Elsevier Ltd. All rights reserved. 
Anthracene; 1-Anthrol; 2-Anthrol; Dehydroxymethylation; Anthracene carbaldehyde