Anomalous reaction products from the alkylation of the disodium adduct of benzophenone anil

Abstract

Treatment of the disodium adduct of benzophenone anil with isopropyl bromide produced substantial amounts of a by-product as well as the previously reported product, 2-methyl-N,1,1-triphenylpropylamine. This by-product is shown to be N(o-isopropylbenzhydryl)aniline, formed by alkylation of the adduct on the aromatic ring.The structural proof relies both upon the synthesis of the unknown amine and upon the oxidation of the unknown amine to o-isopropylbenzophenone.

Bisdecarbonylation of o-carbomethoxybenzoylpentocarbonylmanganese(I)

“…Within 10 min all material had sublimed to a cold finger. Preparative thin-layer chromatography (silica gel, benzene) followed by sublimation (70°, 0.1 mm) gave 0.05 g (66%) of 2a: mp 115-120°dec; uv Xmax(hexane) 210 (sh, e 29,40 ), 234 (« 22,800), and 352 nm (e 2760); m/e 302 (9), 246 (6), 218 (20), Anal. Caled for CnHvMnOs: C, 47.71; H, 2.33; Mr.. 18.18.…”

Iminyls. Part 4. Intramolecular abstraction of benzylic hydrogen by diaryliminyls

“…187-189" (from benzene) (Found: C, 80.2; H , 5.7; N, 6.7. C,,H,,N,O, requires C, 80.0; H, 5.75; N, 6.65y0), 6 3.69 (6 H, s, 2Me0) and 6.88-7.58 (18 o-Benzyldiphenylmethyleneamino-oxyacetic acid ( 1.38 g) gave (i) 1,3-diphenyl-N-( 10-phenyl-9-anthry1)isoindole ( 3 430 and 1 650 cm--l, 6 3.15 (1 H, s, OH), 7.13-7.64 (11 H , m, ArH), 8. 19 (2 H, dd, 1-, 8-ArH); and (v) unchanged acid (430 mg).…”

Alkali metal adducts of benzophenone azine. I. The sodium and potassium adducts

“…In addition, our studies of the reaction of azomethines with alkali metals, (2)(3)(4)(5)(6) have not yet included a molecule with two such groups in conjugation. Our observations to date are incompatible with the earlier report.…”