58940-85-5Relevant academic research and scientific papers
A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)
Kim, Kyoung-Mahn,Park, In-Hwan
, p. 2641 - 2644 (2007/10/03)
Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of
Oxidation of α,β-enones and alkenes with oxone and sodium halides: A convenient laboratory preparation of chlorine and bromine
Dieter, R. Karl,Nice, Lois E.,Velu, Sadanandan E.
, p. 2377 - 2380 (2007/10/03)
Mixtures of oxone and sodium chloride or sodium bromide afford solutions of chlorine or bromine, respectively. These solutions effectively add chlorine and bromine to α,β-enones and alkenes. The method affords improved yields of 3-alkyl-2-halo-2-cycloalkenones which are sometimes difficult to prepare.
Chlorination of α,β-Unsaturated Ketones and Esters in the Presence of Acid Scavengers
Heasley, Victor L.,Elliott, Stephen L.,Erdman, Paul E.,Figueroa, Daphne E.,Krosley, Kevin W.,et al.
, p. 393 - 399 (2007/10/02)
The chlorination of a series of α,β-unsaturated ketones and esters by Cl2 in CH3OH, with and without acid scavengers such as N-chlorosuccinimide (NCS), pyridine and 2,6-lutidine, is described.Methyl vinyl ketone and cyclohex-2-enone have also been chlorinated in ethanol.Mixtures of Markovnikov(M) and anti-Markovnikov(AM) methoxy chlorides and dichlorides are formed in most cases; phenyl vinyl ketone gives no M products in the absence of pyridine, M methoxy chloride is not formed with (E)-4-chlorobut-3-en-2-one under any conditions, pyridine has no effect on the product ratios and methyl 3-chlorobut-2-enoate forms only dichloride.Chlorination of the ketones in the presence of the pyridines results in a significant increase in the M regioisomer (except for methyl isopropenyl ketone and the ketones mentioned), giving M : AM ratios which are similar to the corresponding esters.Ratios for the esters are not affected significantly by pyridine.We ascribe the effect of the pyridine bases to the elimination of acid and the acid-catalysed mechanism, permitting the chlorination to occur via a carbon-carbon ?-bond (chloronium ion) mechanism.The rate of chlorination of methyl vinyl ketone is retarded by pyridine but is still considerably faster than methyl acrylate.NCS, in contrast to N-bromosuccinimide (NBS) reported previously, has no effect on the M : AM ratio.The chlorination of methyl vinyl ketone with NCS and HCl gives markedly different results from Cl2.
