A study of the electronic effects of various substituents on the course of an aromatic cyclodehydration reaction vs. a Elbs-type reaction
Thornton, James Robert
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The acld-oata17zed oyclodehydrat1on reaotion ot 2-benzylphenyl l-naphthyl ketone gives two produots! 9-(1-naphthyl)anthracene, the expected product and 1n addition lO-phenyl-l,2-benzanthracene. Th1s seoond produot 1s the one expeoted it the ketone were subjeoted to the conditions of an .Elba reaotion. The effect of subst1tuents on the oourse ot this reaction was investigated b7 synthesizing six 2-benzylphenyl 1- and 2-naphthyl ketones and subjeoting eaoh of them to the acid oatalyzed reaotion and to Elba reaotion condit1ons. Of the six ketones, two had unsubstituted benzyl groups, two had 3'-methyl groups in the benzyl group and the remaining two had ,'-tr1fluoromethyl groups. fhe original f1nding was oonfirmed and the other ketones that cyollzed by either treatment gave the expeoted products. When 2-(3'-methylbenzyl) 2-naphthl1 ketone was sub3eoted to Elbs reaction con.ditions, 9-(2-naphthyl)anthraoene, the produot of aromatio oyclodehydrat1on, was obtained. An explanation ot the unusual experimental results is suggested. The results of treat1ng the ketones w1th alumina and w1th l1qu1d hydrogen fluoride are reported.
- Doctoral Dissertations