The crystal structures of 1,3-Diphenylpropane-1,2,3-trione, 1,4-Diphenylbutane-1,2,3,4-tetraone, 2,4-Dihydroxy-2,5-diphenylfuran-3(2H)-one and 3,3-Dihydroxy- 1,4-diphenylbutane-1,2,4-trione

Abstract

As a contribution towards a study of the relative disposition of adjacent carbonyl groups in polycarbonyl compounds, the crystal structures of 1,3-diphenylpropane-1,2,3-trione (1), 1,4-diphenyl- butane-1,2,3,4-tetraone (3), 2,4-dihydroxy-2,5-diphenylfuran-3(2H)-one (benzoylformoin) (7) and 3,3-dihydroxy-1,4-diphenylbutane-1,2,4-trio (8) have been determined by X-ray diffraction from diffractometer data at 295 K and refined by least-squares techniques to residuals of 0.036 (942 'observed' reflections), 0.029 (979), 0.067 (941) and 0.045 (1661), respectively. Crystals of 1,3-diphenylpropane-1,2,3-trione are triclinic, P1, a 9.756(4), b 8.813(3), c 8.303(3) �,α 68.56(2), β 67.53(3), γ 89.11(3)�, Z 2. Crystals of 1,4-diphenylbutane-1,2,3,4-tetraone are monoclinic P21/c, a 10.641(2), b 8.381(2), c 14.710(4) �, β 91.70(2)�, Z 4. 2,4-Dihydroxy-2,5- diphenylfuran-3(2H)-one also forms monoclinic crystals, P21/c, a 5.741(4), b 9.276(7), c 24.31(2) �, β 106.26(5)�, Z 4. Crystals of 3,3-dihydroxy-1,4-diphenylbutane-1,2,4-trine are triclinic, P1, a 13.08(1), b 12.43(1), c 8.895(8) �, α 82.54(8), β 81.87(7), γ 78.61(7)�, Z 4.

The Chemistry of Vicinal Polycarbonyl Compounds

“…X-ray structures of a considerable number of triketones have been reported ,,− since the earlier review when only indanetrione ( 4a ) 168 and alloxan ( 110 , R = H) 167 had been determined. The compounds which have been investigated in this way are shown in Charts and .…”

“…The torsion angles between CO groups in the open chain triketones, diphenyl triketone ( 1a ), , dimesityl triketone ( 1c ), and di- p -bromophenyl triketone ( 1b ) 32 varied between 110° and 154°. A further point of interest with these compounds is the torsion angles between the aromatic end groups and their neighboring carbonyl groups.…”

“…Four X-ray structures of tetraketones have been reported (see Charts and ) to date: diphenyl tetraketone ( 2a ), dimesityl tetraketone ( 2c ), 4,4,9,9-tetramethyl[12]paracyclophane-5,6,7,8-tetrone ( 84 ), and 4,4,9,9-tetramethyl-1-oxacycloundecane-5,6,7,8-tetrone ( 85 ) . The most relevant structural data are listed in Table .…”

Photochemistry of Diaryl Vicinal Tetraketones and Chemistry of Intermediate (Aroyloxy)arylketenes1

“…Our attempts and those of others to observe light emission from tetraketones failed to detect either fluorescence or phosphorescence. Structures of 1a and 1d have been determined by X-ray crystallography …”

Configurational and Conformational Mobility in a Cross-Conjugated Derivative of 1,3-Diketo-2-iminopropane

“…We can implicate the syn-E - III structure as being more important than the syn-Z- III structure since our previous observations, , with several model compounds, show that an s-trans -configuration for conjugation is preferred in order to avoid lone pair repulsions. The anti-Z- III and syn-Z- III configurations are implicated as being part of the equilibrium based upon the observation that the crystal structure of the parent III , 1,3-diphenyl-1,2,3- propanetrione, exhibits a skewed conformation that is between and closely aligned to these configurations . Unfortunately, we were unable to directly observe the proposed equilibrium involving anti-Z- III with syn-Z- III or syn-E- III .…”