Anthracenecarboxylic acids

Anthrabarrelene was prepared by generating anthracyne, from 2-amino-3-anthracenecarboxylic acid, in the presence of benzene<60) ... 

More R, Busse G, Hallmann J, Paulmann C, Scholz M, Techert S (2010) Photodimerization of crystalline 9-anthracenecarboxylic acid a nontopotactic autocatalytic transformation. J Phys ChemC 114 4142 148... 

There are several reports wherein head-head dimers were not formed preferentially in micellar solutions. For example, the syn head-tail simers, 61, the same ones obtained in solution formed when a number of 7-al-koxycoumarins (60) (alkoxy group chain length was varied between methoxy to octadecyloxy) were irradiated in SDS and HDTC1 micelles [194,195], The same head-tail dimers, obtained in solution, were formed when 9-methyl-anthracene and 9-anthracenecarboxylic acid were irradiated in CTAB and... 

Figure 10 The y-CD template method for stereoselective preparation of photodimers of 1-anthracenecarboxylic acid.

NX 2-ANTHRACENECARBOXYLIC ACID, 9, lO-DIHYORO-9,10-010X0-7-(alpha-D-GLUC0PYRAN0SYL)-l-HETHYL-3 5.6,6-TETRAHYOROXT-, SODIUH SALT... 

HI - 2-ANTHRACENECARBOXYLIC ACID, 7-alpha-D-GlUCOPYRANOSYL-9,10-DIHYORO-3,5,A,5-TETRAHYDROXY-l-METHYL-9,10-DIOXO-, MONOLITHIUM SALT... 

SYNS 2-ANTHRACENECARBOXYUC ACID, 9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO- 2-ANTHROIC ACID, 9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO- 9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO-2-ANTHRACENECARBOXYLIC ACID CASSIC ACID CHRYSAZIN-3-CARBOXYL1C ACID MO.NORHEIN RHEICACID RHEIN... 

Figure 13. The photochemically induced dethreading (MeCN or H2O, 298 K) of pseudorotaxane [25 4] + based on the use of the external photosensitizer P (e.g., 9-anthracenecarboxylic acid) and the reductant scavenger Red (triethanolamine). Rethreading occurs upon oxygenation of the solution [35, 36].

Carboxylate-bridged Cr dimers are synthesized from chromocene. Benzoic acid, pivalic acid, and 9-anthracenecarboxylic acid react with (f/ -CsH5)2Cr to form Cr2(02CR)4 dimers. Chromium hexacarbonyl is oxidized to dimeric Cr(II) complexes by 2,4-dimethyl-6-hydroxypyrimidine and A, A -(3,5-xylyl) formamidine in refluxing... 

To our knowledge, only one report exists in which the formation of carboxylic acid by radical carboxylation with carbon dioxide has been documented. Curran and co-workers observed the formation of 9-anthracenecarboxylic acid in 10% yield, together with 71% yield of anthracene, when the radical reduction of 9-io-doanthracene with the ethylene-spaced fluorous tin hydride was run using supercritical CO2 (90°C, 280 atm) as the reaction media (Scheme 4-41) [69], As demonstrated in this example, the CO2 trapping reaction by radicals is not an efficient process and therefore is of limited synthetic utility. The rate constant for the addition is yet to be determined, but kinetic studies to date indicate that generally the decarboxylation of acyloxyl radicals is a rapid process [70]. 

Photoinitiated SET has been used to drive a molecular machine and absorption and fluorescence spectroscopy have been used to monitor it. A 1 1 pseudoro-taxane forms spontaneously in solution as a consequence of the donor-acceptor interactions between the electron-rich naphthalene moiety of the thread (380) and the electron-deficient bipyridinium units of the cyclophane (381). The threading process is monitored by the appearance of a charge transfer absorption band and disappearance of the naphthalene fluorescence. Excited state SET from 9-anthracenecarboxylic acid (9-ACA) reduces a bipyridinium moiety of the cyclophane, lessening the extent of interaction between the thread and the cyclophane and dethreading occurs. On addition of oxygen the reduced cyclophane is reoxidised and threading reoccurs. ... 

Photochemical [2+2] cycloaddition of alkenes in the crystalline state is synthetically very useful because it usually produces only one stereoisomer predicted ftom the crystal structure. On the other hand, this stereospeciflcity of the reaction can be a disadvantage because of inaccessibility to other stereoisomers. In order to circumvent such a problem, we explored compelled orientational control of the photodimerization of particular compounds like ranj-cinnamic acids and anthracenecarboxylic acids [74-78]. During our study, photochemistry of fluoro- and chloro-substituted ranj-stilbene-4-carboxylic acids and their methyl esters and alkaline and alkaline earth salts in the crystalline phase was likewise studied in order to synthesize specific stereoisomers selectively (Scheme 41) [79]. Most of these stilbene compounds dimerized to give exclusively or mainly syn head-to-head cyclobutane dimers. Some were photochemicaUy inert. 

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