Reactions of cupric halides with organic compounds—VII
作者:A.D. Mosnaim、D.C. Nonhebel、J.A. Russell
DOI:10.1016/s0040-4020(01)98790-3
日期:1970.1
9-Alkoxy(or acyloxy)-10-methylanthracenes undergo reaction with cupric halides at the Me group to give coupled products, whereas 9-alkoxy(or acyloxy)-10-benzyl(or ethyl)anthracenes react at the alkoxy or acyloxy group to afford 10-benzyl- and 10-ethylideneanthrones respectively. Both types of reaction are postulated to proceed by a radical mechanism.
A competition between normal substitution and tele-substitution is observed with 9-bromoanthracenes bearing in the opposite meso position an ethyl, 1b, or a benzyl group 1d. When treated with potassium phenoxide in HMPT these bromides afford mixtures of 9-alkyl-10-phenoxy-anthracenes 2 and 9-(α(phenoxyalkyl) anthracenes 3. On the other hand 9-bromo-10 isopropylanthracene 1c is quite unreactive and