73453-83-5Relevant academic research and scientific papers
Synthesis of Nuclear Monobromobenzanthracenes
Newman, Melvin S.,Hussain, N. Shoukath
, p. 2837 - 2840 (2007/10/02)
The syntheses of 2-bromo-, 5-bromo-, 10-bromo-, and 11-bromo-7-methylbenzanthracenes, of 5-bromo- and 7-bromo-12-methylbenzanthracenes, and 4-bromo- and 9-bromo-7,12-dimethylbenzanthracenes are described.Bromination of 12-methylbenzanthracene
Synthesis of 8-Hydroxy- and 11-Hydroxy-7,12-dimethylbenzanthracenes. Tin(II) Chloride Mediated Reductions
Newman, Melvin S.,Kanakarajan, K.
, p. 2301 - 2304 (2007/10/02)
8-Methoxybenzanthracene-7,12-dione (3) and 11-methoxybenzanthracene-7,12-dione (4) were converted in high yields to the corresponding 7,12-bis(epoxides) (14a and 14b) (not isolated because of instability) by treatment with the ylide formed from trimethylsulfonium iodide.Reduction with lithium aluminium hydride afforded 7,12-dihydro-7,12-dihydroxy-8-methoxy-7,12-dimethylbenzanthracene (5) and 7,12-dihydro-7,12-dihydroxy-11-methoxy-7,12-dimethylbenzanthracene (6), respectively, in excellent yields.Treatment of 5 and 6 with stannous chloride and hydrogen chloride (or hydrochloric acid) in ether, ethyl acetate, dioxane, and tetrahydrofuran gave over 90percent yields of 8-methoxy-7,12-dimethylbenzanthracene (1) and 11-methoxy-7,12-dimethylbenzanthracene (2), respectively.A discussion of the mechanism of these reductions focuses on the formation of an organotin intermediate and not a free carbenium ion.
