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42%). The latter structure was based on the nmr spectrum of the crude reaction product which showed a quartet at 6.09 (J = 7.5 Hz, vinylic) and a doublet at 2.12 ppm (J = 7.5 Hz, C/73CH=) and formation of 9-isopropyl-10-ethylanthracene from acid-catalyzed rearrangement of the crude product. Isomerization took place under the conditions employed in the preceding example to afford a crude product (0.61 g) shown by glpc and nmr to contain 9-isopropyl-10-ethylanthracene (40%). Chromatography on alumina followed by crystallization from petroleum ether gave pure 9isopropyl-10-ethylanthracene: mpllO-1110; nmr(CC14) 1.45(t, 3,

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icals have, in fact, been photolytically generated from secondary amines in strongly acidic media.16 Parallelling our present results, spontaneous production of aminium radicals from protonated chloramines under mild conditions was observed,16 and subsequent fast addition to unsaturated hydrocarbons. If ordinary aliphatic aminium radicals are generated in weakly basic, neutral, or weakly acidic aqueous media, we have found,17 rapid loss of a protons occurs with subsequent oxidative dealkylation. Hence, the characteristic reactions of aminium ions near neutrality are different from those in strongly acidic media. Experimental SectionWater and triethylenediamine perchlorate were purified as previously described.1 Aqueous hypochlorous acid solutions (16) W.