Compounds III and IV.-To a paste of 30 mg. of I in chloroform was added excess hydriodic acid (sp. gr. = 1.7). After refluxing for 1 hr., the dark red crystalline material had changed to a fine emerald green solution. The solution was cooled, diluted with water, and extracted with chloroform. The chloroform layer was washed with a saturated sodium thiosulfate solution and water, dried over anhydrous sodium sulfate, and concentrated to dryness; 25 mg. of the crude product was obtained. Recrystallization from chloroform afforded III as dark red needles, m.p. >300°. Further purification of III was carried out by acetylation with a mixture of acetic anhydride and pyridine. The acetate (IV) of I was recrystallized from benzene and dried at 160°for 20 hr. under high vacuum; m.p. 295-297°.Anal. Caled, for C46H3402o: C, 60.91; H, 3.77. Found: C, 61.00; H, 3.48. Erythroglaucin (V).-To a suspension of 10 mg. of finely powdered I in 50 ml. of saturated sodium carbonate solution was added 500 mg. of sodium dithionite (under nitrogen). The solution was warmed on a boiling water bath for 10 min. After removal of unchanged I by filtration, the filtrate was acidified with hydrochloric acid and the acidic solution was extracted with benzene.

NotesYol. 27 colorless needles separated at once; yield, 4.0 g. (93%).Sublimation in vacuo gave faintly yellow, sturdy crystals, m.p. 189-190°. A mixture melting point determination with the material prepared by method A showed no depression, and infrared spectra were identical.Treatment of the Complex (IV) with Acetic Anhydride.-A mixture of 1.1 g. of IV, 8 ml. of acetic anhydride, and 10 ml. of pyridine was heated on a steam bath for 40 min. and then evaporated to dryness under reduced pressure.Treatment of the crystalline residue with about 60 ml. of pentane and filtration gave a solid which was recrystallized from carbon tetrachloride to yield 0.46 g. (60%) of long needles, m.p. 115-120°. Sublimation raised the melting point to 118-120°. Diacetylhydroquinone is reported to melt at 123°.10The infrared spectrum of the sublimed material [Nujol mull, principal bands at 5.49 (w), 5.67 (s), 5.80 (sh), and 6.66 µ] was identical with the spectrum of an authentic sample of hydroquinone diacetate.The pentane filtrate was concentrated to a small volume, cooled, and filtered to give a solid (m.p. 91-104°) which was sublimed in vacuo to give 0.45 g. (70%) of 2,3-dimethylquinoxaline, m.p. 103-104°( lit.,11 m.p. 106°). Its infrared spectrum was identical with the spectrum of an authentic sample of 2,3-dimethylquinoxaline.Treatment of the Complex (IV) with Potassium Permanganate.-To a stirred mixture of the complex in aqueous acetone was added solid potassium permanganate until the purple color just persisted. The manganese dioxide was removed by filtration and rinsed with water followed by acetone, and the filtrate was extracted twice with ether.