Commercial soybean lipoxygenase may be used under carefully controlled reaction conditions to give high yields of lipid hydroperoxides. Lipid hydroperoxides so derived from gamma-linolenic or arachidonic acid may be purified by high pressure liquid chromatography. Thus, commercial lipoxygenase serves as a viable source for 100 mg quantities of lipid hydroperoxides.

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The yield was 10% as determined by glpc. Several other unidentified substances were present in very small amounts.Subjection of the brown semisolid to chromatography on a 10 X 1 in. column of alumina using hexane as the eluting solvent and adding benzene as the chromatography proceeded produced 0.29 g (50%) of 2,2'-azoxynaphthalene: mp 163°(lit.30 mp 164°); nmr (CDCls) 7.2-8.2 (aromatic); ir (KBr) 1475 cm"1 (N=NO).Reaction of 7V-(2-Biphenyl)hydroxylamine (11) with Hydrogen Fluoride. Freshly prepared 11 (1.82 g, 9.8 mmol) was slowly added to 100 ml of freshly condensed hydrogen fluoride at -60°.The mixture initially showed a blue color which changed to black after standing for several hours. After evaporation of the hydrogen fluoride, water (30 ml) and ether (30 ml) were added and the contents were neutralized with ammonia gas. The mixture was filtered to give a dark brown residue. The residue was shown to be carbazole ( 23) by comparison of its mass spectrum, infrared spectrum, and thin layer chromatography (silica gel) R¡ data with those of an authentic sample of carbazole. The crude yield was 0.25 g (15%).The filtrate was extracted with ether. The separated organic mixture was dried (MgSO