The Reaction of Iodine with Some Ketones in the Presence of Pyridine

Abstract

hard, gray cake. The yield of crude product was 64.2 g. (0.42 mole), or 85% based on the isopropyl halides.The boiling points of a middle fraction of redistilled material at various pressures were obtained by distillation of a sample through a short Stedman column. The relation between temperature and pressure (in mm.) is given to within ±1.0 mm., which is within the accuracy of the measurements, by the equation log P -7.987 -1858/(/ + 230).Di-s-butylzinc.-By a procedure similar to that described above, di-i-butylzinc was prepared from 68.5 g. (0.5 mole) of i-butyl bromide, 92.0 g. (0.5 mole) of s-butyl iodide, and 140 g. (132 g. Zn, 2.0 g. atom) of zinc-copper couple. The starting temperature was 60°, and the reaction temperature 25°. The yield of crude product was 64.5 g. (0.36 mole), or 72%. On redistillation, the material distilled at 56°at 4 mm.Anal. Caled, for (C«H,)2Zn: Zn, 36.4. Found: Zn, 36.1.

Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents

“…Reaction of ketones 24 with iodine and pyridine under the conditions of the King reaction gave pyridinium salts 25 , which upon basic hydrolysis and acidification provided acids 22 . 24 For purification acids 22 were converted to the corresponding methyl esters under standard conditions and the esters were purified by chromatography. Basic hydrolysis and acidification provided pure acids 22 .…”

Chiral Aryl Pyridyl Alcohols as Enantioselective Catalysts in the Addition of Diethylzinc to Substituted Benzaldehydes

“…47 Additionally, 2acetyl-aromatic compounds were heated with iodine in pyridine at 100-110°C for 3 h and recrystallized from ethanol to produce pyridinium salts. 48,49 Pyridinium salts and a,b-unsaturated ketone were then heated with ammonium acetate in glacial acetic acid at 100-110°C overnight to yield the corresponding pyridines 1-5. 49 Next, compounds 1-4 were treated with LDA at -40°C, and a solution of benzophenone in THF was added to generate the corresponding alcohols 6-9.…”

4,5-Dibromo-1,2-dimethyl-1H-imidazol-3-ium bromide

“…For the preparation of the title compound using the Ortoleva-King reaction, see: King (1944). For applications of C,Nsubstituted haloimidazole derivatives, see: Reepmeyer et al (1975); Zamora et al (2003); Schmidt & Schieffer (2003); Mashkovskii (2005); Amini et al (2007).…”