41959-24-4Relevant academic research and scientific papers
Synthesis of tetraarylmethanes via a Friedel-Crafts cyclization/desulfurization strategy
Griffin, Paul J.,Fava, Matthew A.,Whittaker, St. John T.,Kolonko, Kristopher J.,Catino, Arthur J.
, p. 3999 - 4002 (2018)
Tetraarylmethanes are an important class of molecules that contain four aryl groups bonded to a central carbon atom. The shape/three-dimensionality of these molecules makes them suitable for organic light-emitting diodes (OLEDs), organic solar cells, hydrogen storage, and even drug-delivery. Despite their importance, there are only a few methods available for their preparation. Herein, we report a simple procedure for the preparation of tetraarylmethanes that involves a bismuth-catalyzed Friedel-Crafts cyclization followed by a desulfurization reaction mediated by Raney nickel.
Reactions of 9-phenylthioxanthene 10-oxide with organometallic reagents
Shimizu,Kataoka,Hori
, p. 842 - 845 (2007/10/02)
Reactions of 9-phenylthioxanthene 10-oxide (1) with a variety of Grignard reagents afforded 9-substituted 9-phenylthioxanthenes (2). Similarly, organolithiums reacted with the sulfoxide 1 to give the corresponding thioxanthenes 2. The structures of 9-aryl
REACTIVITIES OF HETEROAROMATIC CATIONS CONTAINING A GROUP VIB ELEMENT IN NUCLEOPHILIC REACTIONS. REACTIONS OF 9-PHENYL-XANTHYLIUM, -THIOXANTHYLLIUM, AND -SELENOXANTHYLIUM SALTS WITH AMINES, SODIUM PHENOLATE, AND SODIUM BENZENETHIOLATE
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Hsu, Chen Fu,Hasegawa, Yukio,Eyama, Noriko
, p. 2271 - 2276 (2007/10/02)
Reactions of 9-phenylchalcogenoxanthyllium salts (1a-c) with some nucleophiles have been examined in order to find the differences in reactivity in nucleophilic reactions.The chalcogenoxanthylium salts (1a-c) react with aniline in ether to give 9-anilino-9-phenylchalcogenoxanthenes (7a-c).However, in acetonitrile the xanthylium salt (1a) affords N,4-bis(9-phenylxanthen-9-yl)aniline (9a) together with the anilinoxanthene (7a) (at room temperature) or 9-(p-aminophenyl)-9-phenylxanthene (8a) (at reflux) and the sulphur (1b) and the selenium derivative (1c) affords only the anilino derivatives (7b,c), respectively.In the reactions with sodium phenolate, the thioxanthylium salt (1b) gave 9-phenoxy-9-phenylthioxanthene (13b), whereas the oxygen (1a) and the selenium congener (1c) gave O,4-bis(9-phenylchalcogenoxanthen-9-yl)phenols (15a,c) together with the 9-phenoxy derivatives (13a,c), respectively.The results show that the thioxanthylium salt (1b) gave the products formed on attack by the heteroatom of the ambident nucleophiles and the ratio of the carbon attack increased in the order (1a) > (1c) > (1b).This difference would be attributable to the properties of carbocations at the 9-position in the heteroaromatic cations (1a-c).
Syntheses and Reactions of 9-Substituted 10-Phenylthioxanthenium Salts: Negative Evidence for Thia-anthracene Oligomerisation
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Ikemori, Megumi,Aoyama, Yasuko
, p. 1209 - 1218 (2007/10/02)
Various 9-aryl-10-phenylthioxanthenium salts have been prepared and their stereochemistry determined by (1)H n.m.r. spectroscopy.Reactions of the 10-phenylthioxanthenium salts or 10-phenyl-10-thia-anthracenes with aryl-lithiums have been studied in order to investigate whether or not 10-thia-antracenes cause oligomerisation.The 10-phenylthioxanthenium salts reacted with aryl-lithiums to give 9-phenylthioxanthenes in good yields.However, 10-phenylthioxanthenium salt (19) when treated with phenyl-lithium at -15 to -20 deg C gave 9-phenylthioxanthenol (38) (17percent) together with 9-phenylthioxanthene (13) because of the lability of 10-phenyl-10-thia-anthracene to air. 10-Phenyl-9-(p-tolyl)-10-thia-anthracene (50) generated in situ from the sulphonium salt (22) and lithium diisopropylamide failed to react with p-tolyl-lithium.An isolable ylide, 9-benzoyl-10-phenyl-10-thia-anthracene (52) was treated with p-tolyl-lithium at 0 deg C to give 9-benzoylthioxanthene (4) (82percent).In contrast, 9,9,10-triphenylthioxanthenium salt (24) on treatment with phenyl-lithium gave a ring-opened product (40), a ring-contracted product (41), diphenylsulphide (42), and 9,9-diphenylthioxanthene (12).These results indicate that the 10-phenyl-thia-anthracenes or the ?-sulphuranes of thioxanthenes do not cause oligomerisation.
