Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol) - PubMed (original) (raw)
Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)
Alexander J Fatiadi et al. J Res Natl Bur Stand A Phys Chem. 1963 Mar-Apr.
Abstract
Reliable procedures are given for the preparation and purification of hexahydroxybenzene (benzenehexol), tetrahydroxy-_p_-benzoquinone, rhodizonic acid, triquinoyl (cyclohexanehexone), croconic acid, and leuconic acid (cyclopentanepentone). Certain derivatives and color tests, as well as infrared and ultraviolet spectra, are reported for their identification.
Figures
Figure 1.. Infrared spectrograms of materials in Nujol mulls.
I, Hexahydroxybenzene; II, tetrahydroxyquinone; III, rhodizonic acid dihydrate. IV, Triquinoyl octahydrate; V, croconic acid trihydratc; VI, leuconic acid pentahydrate.
Figure 1.. Infrared spectrograms of materials in Nujol mulls.
I, Hexahydroxybenzene; II, tetrahydroxyquinone; III, rhodizonic acid dihydrate. IV, Triquinoyl octahydrate; V, croconic acid trihydratc; VI, leuconic acid pentahydrate.
Figure 2.. Ultraviolet spectrograms of materials.
I. Hexahydroxybenzene. Curve A, 7.39 mg of I in 100 ml of 6_N_ HCl in methanol, 3 min after dissolution; λmax at 278 m_μ_. Curve B, 67 mg of the hexaacetate of I in 200 ml of glacial acetic acid, 10 min after dissolution; λmax at 263 m_μ_. II. Tetrahydroxyquinone. Curve A, 3.82 mg of II in 1000 ml of 2_N_ aqueous HCl, 24 hr after dissolution; λmax at 308 m_μ_. Curve B, 7 mg of II in 1000 ml of methanol, 30 min after dissolution; λmax at 312 m_μ_. III. Rhodizonic acid dihydrate. Curve A, 6.87 mg of III in 1000 ml of 2_N_ aqueous HCl 24 hr after dissolution; λmax at 235 m_μ_ and at 319 m_μ_. Curve B, 8.58 mg of III in 1000 ml of methanol, 5 min after dissolution; λmax at 235 m_μ_ and at 323 m_μ_. In the visible region, III shows absorption at 443 m_μ_ and at 487 m_μ_ (sh). IV. Triquinoyl octahydrate. 3.24 mg of IV in 100 ml of 2_N_ aqueous NaCl 1.5 hr after dissolution; λmax at 267 mμ. In the visible region, IV shows marked absorption at 363 m_μ_, 440 m_μ_ (sh) and 480 m_μ_. V. Croconic acid trihydrate. 5.87 mg of V in 100 ml of 2_N_ aqueous HCl, 10 min after dissolution; λmax at 231 m_μ_ and at 298 m_μ_. VI. Leuconic acid pentahydrate. 156.45 mg of VI in 50 ml of water, 5 min after dissolution; λmax at 328 m_μ_.
Figure 2.. Ultraviolet spectrograms of materials.
I. Hexahydroxybenzene. Curve A, 7.39 mg of I in 100 ml of 6_N_ HCl in methanol, 3 min after dissolution; λmax at 278 m_μ_. Curve B, 67 mg of the hexaacetate of I in 200 ml of glacial acetic acid, 10 min after dissolution; λmax at 263 m_μ_. II. Tetrahydroxyquinone. Curve A, 3.82 mg of II in 1000 ml of 2_N_ aqueous HCl, 24 hr after dissolution; λmax at 308 m_μ_. Curve B, 7 mg of II in 1000 ml of methanol, 30 min after dissolution; λmax at 312 m_μ_. III. Rhodizonic acid dihydrate. Curve A, 6.87 mg of III in 1000 ml of 2_N_ aqueous HCl 24 hr after dissolution; λmax at 235 m_μ_ and at 319 m_μ_. Curve B, 8.58 mg of III in 1000 ml of methanol, 5 min after dissolution; λmax at 235 m_μ_ and at 323 m_μ_. In the visible region, III shows absorption at 443 m_μ_ and at 487 m_μ_ (sh). IV. Triquinoyl octahydrate. 3.24 mg of IV in 100 ml of 2_N_ aqueous NaCl 1.5 hr after dissolution; λmax at 267 mμ. In the visible region, IV shows marked absorption at 363 m_μ_, 440 m_μ_ (sh) and 480 m_μ_. V. Croconic acid trihydrate. 5.87 mg of V in 100 ml of 2_N_ aqueous HCl, 10 min after dissolution; λmax at 231 m_μ_ and at 298 m_μ_. VI. Leuconic acid pentahydrate. 156.45 mg of VI in 50 ml of water, 5 min after dissolution; λmax at 328 m_μ_.
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