138002-07-0Relevant academic research and scientific papers
Bromolysis and iodolysis of α,β-epoxycarboxylic acids in water catalyzed by indium halides
Amantini,Fringuelli,Pizzo,Vaccaro
, p. 4463 - 4467 (2007/10/03)
The ring opening of α,β-epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-β-monoalkylated epoxycarboxylic acids at pH 4.0 was completely α-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of α,β-epoxycarboxylic acids at pH 1.5 gave the corresponding anti β-iodohydrins in 88-95% yields. The one-pot synthesis of the α- and β-hydroxyhexanoic acids, starting from the corresponding α,β-epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.
Dihydroxyacids from the chlorination of ketones: an unexpected process
Guthrie, J. Peter,Cossar, John,Lu, Jinqiao
, p. 1904 - 1908 (2007/10/02)
Chlorination of propiophenone in aqueous alkali at room temperature, with low concentrations of hypochlorite, leads to 2-phenylglyceric acid as the major product.This acid is formed by further oxidation of 1-phenyl-1,2-propanedione, which is an intermediate in the oxidation of propiophenone.Formation of this acid is reasonable in the light of other halogenation chemistry.Analogous reactions are observed for butyrophenone, which yields 2,3-dihydroxy-2-phenylbutanoic acid, and for cycloheptanone, which yields 1,2-dihydroxycyclohexanecarboxylic acid. Key words: 2-phenyl glyceric acid, propiophenone, chlorination, hydrolysis, rearrangement, cycloheptanone, 1,2-dihydroxycyclohexanecarboxylic acid.
