13417-34-0Relevant academic research and scientific papers
Use of Magnesium Anthracene * 3 THF in Synthesis: Generation of Grignard Compounds and Other Reactions with Organic Halides
Bogdanovic, Borislav,Janke, Nikolaus,Kinzelmann, Hans-Georg
, p. 1507 - 1515 (2007/10/02)
The course (a), (b), (c) (Scheme 1) of the reaction of magnesium anthracene * 3 THF (1) with organic halides (RX) is dependent on the nature of RX.With alkyl halides in THF 1 reacts as a nucleophile, whereby primary as well as secondary alkyl halides produce dialkyldihydroanthracenes (4-4'') and tertiary alkyl halides yield primarily monoalkyl-substituted dihydroanthracenes (2, 2').With bromo- and iodobenzene in THF 1 reacts predominantly as a radical with H atom abstraction from the solvent affording benzene and 9.The formation of Grignard compounds (5) and anthracene (6), originating from primary and secondary alkyl and aryl halides and 1 in toluene or ether at elevated temperatures, is not caused by the reaction of 1 but by the "active magnesium" (Mg*) formed by decomposition of 1 in these solvents.In contrast, allyl, propargyl, and benzyl halides react with 1 independently of the solvent under mild conditions to produce 5 and 6.Allyl- and the difficultly accessible allenylmagnesium chloride can be prepared in THF at -78 and 0 deg C, respectively, from the corresponding halides and ordinary Mg powder via catalytic amounts of 1.
Synthesis of 9-Methylene-9,10-dihydroanthracene by Lithium Aluminium Hydride Reduction of (9-Anthrylmethyl)trimethylammonium Chloride
Takagi, Masato,Hirabe, Tomoatsu,Nojima, Masatomo,Kusabayashi, Shigekazu
, p. 1311 - 1314 (2007/10/02)
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).
