40476-29-7

Upstream product

• 35818-89-4 (9-anthracenyl-methyl)trimethylammonium chloride 
• 121513-50-6 9-(2-anilinoethyl)anthracene 
• 118246-92-7 N,N-dimethyl-N-(9,10-dihydroanthryl-9-methyl)amine oxide 

Downstream Products

• 779-02-2 9-methylanthracene 
• 723-62-6 anthracen-9-carboxylic acid 
• 116076-83-6 9-(cyclohexylmethyl)-9,10-dihydroanthracene 

Relevant academic research and scientific papers

Photochemical Behaviour of 9-(2-Anilinoethyl)- and 9-(3-Anilinopropyl)anthracenes in Various Solvents

Photochemical reactions of the title compounds and related aniline derivatives have been studied in various solvents.Products isolated from an irradiated mixture of 9-(2-anilinoethyl)anthracene (5) were: 9-methylene-9,10-dihydroanthracene (6), N-phenyl-9,

Bimolecular Reactions of 3-Methylene-1,4-cyclohexadiene (p-Isotoluene), 5-Methylene-1,3-cyclohexadiene (o-Isotoluene), 1-Methylene-1,4-dihydronaphthalene (Benzo-p-isotoluene), and 9-Methylene-9,10-dihydroanthracene (Dibenzo-p-isotoluene)

3-Methylene-1,4-cyclohexadiene, 1, 5-methylene-1,3-cyclohexadiene, 2, 1-methylene-1,4-dihydronaphthalene, 5, and 9-methylene-9,10-dihydroanthracene, 8, react with second-order kinetics in benzene solution.The activation parameters for the reaction of 1,5,and 8, especially the frequency factor, suggest a nonconcerted reaction with little orientational demand in the transition state.The frequency factor for the reaction of 2 suggests a concerted pathway.The product distribution from each compound reinforces the kinetic observations.The products from the pyrolysisof 1 could be rationalized by a radical cage intermediate, which could combine or disproportionate.The reaction products from 5 indicate a radical chain oligomerization.The reaction of 8 gives an insoluble solid. o-Isotoluene (2) gives ene dimers.

Synthesis of 9-Methylene-9,10-dihydroanthracene by Lithium Aluminium Hydride Reduction of (9-Anthrylmethyl)trimethylammonium Chloride

Treatment of (9-anthrylmethyl)trimethylammonium chloride (2a) with 1 mol equiv. of lithium aluminium hydride (LAH) in refluxing tetrahydrofuran gave predominantly 9-methylene-9,10-dihydroanthracene (3a).However, reaction with 3 mol equiv. of LAH gave a mixture of 9-methyl-9,10-dihydroantracene (5a) and 9-(9-anthrylmethyl)-9-methyl-9,10-dihydroanthracene (6a), these products being formed by processes involving nucleophilic attack of excess of LAH on compound (3a).