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Pregled bibliografske jedinice broj: 888778

Synthesis of asymmetrically disubstituted anthracenes


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 (međunarodna recenzija, članak, znanstveni)


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


Projekt / tema
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )
HRZZ-UIP-02.05/25 - Fotokemija policikličkih molekula: od istraživanja mehanizma reakcije do novih lijekova i medicinskih primjena (Nikola Basarić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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