17239-99-5Relevant academic research and scientific papers
Hydrogenation of Aromatic Hydrocarbons by Al/Ti Reagents
Yalpani, Mohamed
, p. 983 - 987 (2007/10/02)
Treatment of anthracene (A) with LiAlH4 (LAH) at 150 deg C under atmospheric pressure gives 9,10-di- and 1,2,3,4-tetrahydroanthracene (2H-A and 4H-A).At 160-200 deg C and under hydrogen pressure (10-90 bar) a number of simple and polycyclic aromatic compounds are converted to fully or partially hydrogenated arenes.Addition of small amounts of TiCl4 or TiCl3 and the choice of solvents (heptane or glymes) have marked effects on the reaction.The pair triethylaluminium/TiCl4 acts also as efficient hydrogenation catalyst.
Reactions with Aziridines, 45. - Arene Hydrides, 5 Reversibility of Carbonyl Attack on N-Benzoylaziridines Prior to Ring Opening by Carbanions. - Strong Influence of the Gegen Ion
Mall, Thomas,Stamm, Helmut
, p. 1349 - 1352 (2007/10/02)
A previous report had shown that anthracene hydride AH- or the xanthenyl anion X-, respectively, at first add to the carbonyl group of N-benzoylaziridines since high yields of benzoyl dihydroanthracene 3 or benzoyl xanthene 11 were obtained when in early stages the reaction was quenched with protons.The respective intermediate carbonyl adducts 2 and 10 had been considered to be precursors of products resulting from homolysis of the aziridine ring.It is now shown that quenching of the reaction between AH- or X- and N-benzoylaziridines 1a, b with methyl iodide or aroyl chlorides results in substantial yields of products derived from either AH- (or X-) or 1a,b.This indicates that 2 (or 10) are in equilibrium with AH- (or X-) and 1a, b.Study of the gegen ion influence with X- revealed that the equilibrium concentrations of 10-Na+ were much lower than those of 10-Li+ while simultaneously the ring opening of 1a was distinctly faster with X-Na+ than with X-Li+.This finding suggests that, contrary to the previous assumption, the equilibrium concentrations, of X- and 1a are responsibile for the (homolytic) ring opening.
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).
