14596-75-9

Upstream product

• 60-29-7 diethyl ether 
• 17803-81-5 10-phenyl-9-acetoxyanthracene 
• 75-16-1 methylmagnesium bromide 
• 52236-50-7 10-chloro-10-phenyl-anthrone 
• 60079-98-3 10-phenyl-9-anthracene-ol 
• 77130-68-8 dimethylamino-9 epidioxy-9,10 phenyl-10 dihydro-9,10 anthracene 
• 77130-69-9 N,N-Dimethyl hydroperoxy-10 methoxy-9 phenyl-10 dihydro-9,10 anthraceneamine-9 
• 602-50-6 2-(diphenylmethyl)benzoic acid 
• 21620-42-8 anthrone-10-spiro-3'-3'H-indazole 
• 602-55-1 9-phenylanthracene 
• 14596-70-4 10-phenylanthrone 

Downstream Products

• 5146-30-5 10-phenyl-10-hydroxy-9-anthracenone 
• 84-65-1 9,10-phenanthrenequinone 
• 108-95-2 phenol 
• 875227-10-4 10-methylperoxy-10-phenyl-anthrone 

Relevant academic research and scientific papers

COMPETITION ENTRE SUBSTITUTION NULCEOPHILE ET REDUCTION CHEZ LES BROMO-9 ANTHRACENES DANS L'ACTION DES ANIONS PHENATE ET METHYLATE; APPLICATION A LA MONO-DEUTERIATION SPECIFIQUE EN MESO EN SERIE ANTHRACENIQUE

Treatment of meso-substituted 9-bromoanthracenes bearing no hydrogen in the α position with potassium phenoxide in DMF gives rise to a competition between nucleophilic substitution and reductive dehalogenation.Derivatives carrying electron attracting groups, 1c (Br), 1e (CN) and 1f (NO2), react essentially by substitution leading to phenolic ethers 2, whereas with non-activated bromides, 1a (H), 1b (C6H5) and 1d (OC6H5), the main reaction is a reduction to anthracenes 3 which should arise from an electron transfer.A reduction of 9-bromoanthracene into anthracene is also observed with sodium methoxide and it is shown, by labelling, that this one must result from a hydride transfer from methoxide.It may be applied to the specific meso-monodeuterization of various anthracenic derivatives.

Reactions of Spiro-indazoles containing Keto-groups. Syntheses of Benzaceanthrylenes, Naphthaceanthrylenes, and Fluoranthenes

Anthrone-10-spiro-3'-3'H-imidazole (1) and 3H-indazole-3-spiro-1'-naphthalen-4'(1'H)-one (3), prepared by the cycloaddition of benzyne with 10-diazoanthrone (6) and 4-diazanaphthalen-1(4H)-one (7), respectively, thermally rearranged with elimination of nitrogen to 8-hydroxybenzaceanthrylene (9b) and 3-hydroxyfluoranthene (11b), respectively.The diazoketone (6) reacted with 1,2-naphthyne to give anthrone-10-spiro-3'-3'H-benzindazole (4) and anthrone-10-spiro-1'-1'H-benzindazole (5), which gave the rearrangement product, 10-hydroxynaphthaceanthrylene (12b) by thermolysis.Photolysis of the spiro-indazoles afforded the rearrangement and/or photo-oxidation products.Thermolysis and photolysis are accountable on the basis of formation of biradicals and isomerization of these to fused polycyclic compounds.In particular, the isomerization of the biradical (21) to (12b) involves the formation of the naphthocyclopropene (20).

PHOTO-OXYGENATION D'AMINES AROMATIQUES ENDOPEROXIDES D'AMINO-9 ANTHRACENES

The direct photo-oxygenation of 10-phenyl and 10-methoxy-9-dimethylaminoanthracenes 1a and 1b gives the corresponding 9,10-endoperoxides 2a and 2b.The latter are unstable owing to their high reactivity toward nucleophiles.