21992-33-6Relevant articles and documents
Regioselective alkylation of anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis
Dehmlow, Eckehard Volker,Bollhoefer, Joerg,Thye, Gorden
, p. 113 - 115 (2007/10/03)
Anthrone (1) can be alkylated selectively to give O-, C,O- or C,C-substituted compounds 2, 4, or 5, respectively. Similarly, 5,5-dimethyl-3-isoxazolidinone (6) and 4-methylquinolone (9) yield N- or O-derivatives 7 and 8 or 10 and 11, respectively. The product ratios can be influenced strongly sometimes by use of different phase transfer catalysts, but the sensitivity of each reaction towards the catalysts is unique.
TELE-SUBSTITUTIONS EN SERIE ANTHRACENIQUE-I. COMPORTEMENT DU BROMO-9-METHYL-10 ANTHRACENE VIS-A-VIS DES ANIONS PHENATES ET ALCOOLATES
Rigaudy, J.,Seuleiman, A.M.,Cuong, Nguyen Kim
, p. 3143 - 3150 (2007/10/02)
Treatment of 9-bromo-10-methyl anthracene 1, in dipolar aprotic solvents, by alkaline phenoxide or alkoxides leads essentially to a mixture of the expected ether, 9-phenoxy (or alkoxy)-10-methyl anthracene 2, normal substitution product (NSP), and of the isomeric ether, 9-phenoxymethyl (or alkoxymethyl)-anthracene 3, tele-substitution product (TSP).It is shown that both ethers must derive from a common unstable intermediate, the 9-bromo-10-methylene-9,10-dihydroanthracene 8, coming from 1 by a prototropic shift and which can undergo both types of substitution.With more hindered phenoxide ions, only the tele-substitution process is observed.