Synthesis of New Anthracene Derivatives

Abstract

An efficient synthesis is described for hexabromoanthracenes 3 and 4 by direct bromination of 9,10-dibromoanthrecene 2. Whereas base-induced elimination of hexabromide 3 with t-BuOK gave 2,3,9,10-tetrabromoanthracene 5, the reaction of hexabromide 4 with DBU afforded 1,3,9,10-tetrabromoanthracene 6 as the sole product. Tetrabromide 5 was also obtained by aromatization of 1,4-dinitroxy-2,3,9,10-tetrabromo-1,2,3,4-tetrahydroanthracene 17. Efficient and convenient synthetic routes are described for the preparation of dinotroxy 17, dimethoxy 23, and dihydroxides 18 and 19 with silver-induced substitution of hexabromides 3 and 4. The hydroxy compounds 19 and 18 were converted to diepoxide 20 and monoepoxide 21, respectively, with sodium methoxide. Base-promoted aromatization of dimethoxide 23 afforded dibromomonomethoxides 26 and 27. Bromoanthracenes and isomeric arene oxides constitute valuable precursors for the preparation of functionalized substituted anthracene derivatives that are difficult to prepare by other routes.

2,4-Dibromo-2,3-dihydro-1H-inden-1-yl acetate

“…For bromination of hydrocarbons, see : Catto et al (2010); Erenler & Ç akmak (2004); Erenler et al (2006); McClure et al (2011); Mitrochkine et al (1995); Snyder & Brill (2011);Wu (2006);Ç akmak et al (2006). For puckering parameters, see: Cremer & Pople (1975 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009 Brominations of hydrocarbons are important processes in synthetic chemistry (Çakmak et al, 2006;Erenler et al, 2006;Erenler & Çakmak, 2004).…”

Synthesis, Crystal and Molecular Structure of 2′,3′,3′-Tribromo-2′,3′-dihydrospiro[1,3-dioxolane-2,1′-indene]

“…Brominations of hydrocarbons are important processes in synthetic chemistry [6][7][8][9][10]. The materials obtained from bromination of hydrocarbons have numerous industrial applications as pesticides, plastics, fire retardants and pharmaceutical chemicals [11].…”

Hierachical Self-Assembly of an Anthracene Derivative in Aqueous Solution

“…Among the polycyclic aromatic hydrocarbons, anthracene and its derivatives have been extensively investigated due to bimolecular photochemical and photochromic properties that can be used in the design of optical, electronic, or magnetic switches. 28 Therefore, TPAP has been selected as the self assembly monomer to study the self-assembly behavior. Such complex architectures are undoubtedly interesting in understanding the self-assembling of hierarchical superstructures and helpful to prepare functional architectures.…”