79352-68-4Relevant academic research and scientific papers
Photochemistry of 1, n -Dibenzyloxy-9,10-anthraquinones
Sarma, Saurav J.,Jones, Paul B.
supporting information; experimental part, p. 3806 - 3813 (2010/08/20)
Figure presented The photochemistry of a series of 9,10-anthraquinones with multiple benzyloxy substituents was investigated. In polar solvent, the expected Blankespoor oxidative cleavage reaction is the major reaction pathway, but in most cases, several minor products were observed. In nonpolar solvents, the abundance of these minor products increases dramatically. Four types of product were observed with the favored reaction pathway shifting with minor changes in substitution on the anthraquinone. Several types of product require cleavage of the C-O bond on the benzyloxy group and, apparently, follow a photo-Claisen-type mechanism. Others involve the expected 1,5-diradical but do not exhibit the single-electron transfer usually observed in the Blankespoor-type reaction. The results indicate the importance of considering the medium and photoredox behavior in anthraquinone photochemistry.
Alkynes and Poly(ethylene glycol) Derivatives as Nucleophiles and Catalysts in Substitution Reactions of 1-Chloroanthraquinones
Fang, JunPing,Lu, Tianbao,Kim, Hyunsook,Delgado, Isaura,Geoffroy, Philippe,et al.
, p. 7059 - 7065 (2007/10/02)
Two synthetically useful approaches to 1-substituted anthraquinone derivatives are reported.Application of these methods afforded the following 1-anthraquinyl ethers: n-propyl, n-butyl, n-octyl, n-nonyl, n-hexadecyl, isoamyl, allyl, 2-butenyl, (E)-2-hexenyl, (E)-2-tridecyl, benzyl, phenyl, 4-methylphenyl, 2-butynyl, 2-pentynyl, 2-hexynyl, 3-pentynyl, 3-hexynyl, 3-heptynyl, 3-nonynyl, 4-hexynyl, 4-heptynyl, 5-heptynyl, 5-octynyl, 5-nonynyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl, 2-ethoxy>ethyl, 2-(methylthio)ethyl, 2-(1-piperidino)ethyl, and 2-(1-morpholino)ethyl.The results of about 100 nucleophilic substitution reactions (a number were duplicates) are presented.Most of these reactions involve either a new approach, new products, or both.Includes are displacements of chloride by alkanols, alkenols, and alkynols.Of the three, only the latter afford acceptable yields of product, although lower yields are observed as the distance between hydroxyl and triple bond increases.Nucleophiles of the type RO(CH2CH2O)nOH proved remarkably effective.Alkynyl ethers and poly(oxyethylene) ethers also proved to be excellent leaving groups.Both alkynols and oligoethylene glycol monoethers were found to be catalysts for the conversion of 1-chloroanthraquinone into 1-anthraquinyl ethers.In an attempt to understand the mechanism of this reaction, solid-state structures of four anthraquinone derivatives have been obtained.These have poly(ethyleneoxy), morpholino, or alkynyl side arms.
A New Route to Anthraquinones
Dodsworth, David J.,Calcagno, Maria-Pia,Ehrmann, E. Ursula,Devadas, Bhatt,Sammes, Peter G.
, p. 2120 - 2124 (2007/10/02)
The lithium salts derived from position 3 of phthalides react with arynes to form adducts, which, upon aerial oxidation, produce anthraquinones in moderate to good yields.Substituted phthalides and arynes also participate in this general reaction.The addition to unsymmetrically substituted arynes shows regioselectivity, whilst the availability of a new general route to phthalides extends the scope of this reaction.
