The Photochemical Friedel-Crafts Acylation of Quinones - From the Biginnings of Organic Photochemistry to Modern Solarchemical Applications

Oelgemöller M, Mattay J. The Photochemical Friedel-Crafts Acylation of Quinones - From the Biginnings of Organic Photochemistry to Modern Solarchemical Applications. In: Horspool WM, ed. CRC Handbook on Photochemistry and Photobiology. 2nd. Ed. USA/Boca Raton: CRC Press; 2004: 88-1-88-45

Crystal structure of (4bS,9S) 4b-Hydroxy-11,13-dioxo-4b,7,8,9,10,11,12,13-octahydro-5H-6-thia-10,12a-diaza-cyclodeca[a]indene-9-carboxylic acid methyl ester with a remarkable short S···H contact of 2.61 Å

The title compound was prepared from the N-phthaloyl derivative of the dipeptide glycyl L-methionine by irradiation (300 nm wavelength, 27 hours, 2 mmol in 100 ml of acetone at room temperature). The crude product was purified by column chromatography on silica (methanol/methylene chloride 1:20) which yielded 54% of the diastereoisomerically pure cis compound. The resulting material was dissolved in acetone and after slow evaporation of the solvent, a colorless oil resulted from which tiny and air-sensitive colorless needles crystallized with mp of 468 Κ - 469 Κ

Crystal structure of 1-Hydroxy-2'-methoxy-bicyclohexyl-1'-ene-2,3'-dione

The title compound was formed as a side-product via barium oxide/hydroxide mediated coupling of 1,2-cyclohexanedione, followed by in situ methylation with dimethyl sulfate. Recrystallization from n-hexane gave 11% of colorless prisms (mp 398 Κ - 400 Κ). Main product of this transformation was the methylated monoenolate of the dione in 54% yield

Crystal structure of 1-Hydroxy-2'-methoxy-bicyclohexyl-1'-ene-2,3'-dione

The title compound was formed as a side-product via barium oxide/hydroxide mediated coupling of 1,2-cyclohexanedione, followed by in situ methylation with dimethyl sulfate. Recrystallization from n-hexane gave 11% of colorless prisms (mp 398 Κ - 400 Κ). Main product of this transformation was the methylated monoenolate of the dione in 54% yield

Crystal structure of 4b-Hydroxy-4b, 6, 8, 9-tetrahydro-5H-7-thia-9a-aza-benzo[a]-azulen-10-one

The title compound was prepared from potassium 3-(2-phthalimidoethylsulfanyl)propionate by irradiation in an acetone/water mixture. Extraction and recrystallization from acetone yielded 25% of colorless crystals

Crystal structure of N-cyclooctylidene-N-(2,4-dinitrophenyl)-hydrazine

The title compound was prepared from cyclooctenone and 2,4-dinitrophenylhydrazine in ethanol. Recrystallization from diethylether yielded 85% of yellowish prisms