5170-76-3Relevant academic research and scientific papers
Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism
Jobin-Des Lauriers, Antoine,Legault, Claude Y.
supporting information, p. 108 - 111 (2016/01/15)
An unprecedented iodine(III)-mediated oxidative transposition of vinyl halides has been accomplished. The products obtained, α-halo ketones, are useful and polyvalent synthetic precursors. There are only a handful of reported examples of the direct conversion of vinyl halides to their corresponding α-halo carbonyl compounds. Insights into the mechanism and demonstration that this synthetic transformation can be done under enantioselective conditions are reported.
Investigations into the regioselective C-deuteration of acyclic and exocyclic enolates
Eames, Jason,Coumbarides, Gregory S.,Suggate, Michael J.,Weerasooriya, Neluka
, p. 634 - 641 (2007/10/03)
Results are reported on the regioselective C-deuteration of a series of related acyclic and exocyclic enolates derived from substituted aryl ketones. We comment on factors, such as the presence of additives and the structural nature of the enolate, that influence the observed C-deuteration and discuss the role of the deuterium donor. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
Vinyl Cation Formation by Decomposition of Vinyl-lead Triacetates. The Reactions of Vinylmercury and Vinyltin Compounds with Lead Tetra-acetate
Moloney, Mark G.,Pinhey, John T.,Stoermer, Martin J.
, p. 2645 - 2655 (2007/10/02)
Vinylmercury compounds and vinylstannanes undergo rapid metal-metal exchange with lead tetra-acetate in chloroform to generate vinyl-lead triacetates, unstable compounds which undergo a thermodynamically favourable reductive elimination of lead(II) acetate.In the presence of mercury(II) salts, vinyl-lead triacetates collapse to the corresponding enol acetate, but in the absence of mercury(II) they yield either the enol acetate or an acetylene depending on the substitution at the double bond.Evidence for the formation of vinyl cations in the collapse of a number of vinyl-lead triacetates has been obtained.Strong support for such intermediates comes from the decomposition of (E)-o-methoxystyryl-lead triacetate, where the nature of the participation by the neighbouring methoxy group excluded the possibility of involvement of an alkylidenecarbene.Attempted trapping of an alkylidenecarbene by cyclohexane in the decomposition of 2-methylprop-1-enyl-lead triacetate was also unsuccessful, indicating the absence of such an intermediate.
ACYLATION OF α-BROMINATED KETONES IN THE PRESENCE OF ZINC
Fotin, V. V.,Shchepin, V. V.,Sinani, S. V.
, p. 1744 - 1746 (2007/10/02)
The acylation of α-bromo ketones in the presence of zinc takes place preferentially at the O-reaction center of the intermediate organozinc compound.
Acylation of Ketone Silyl Enol Ethers with Acid Chlorides. Synthesis of 1,3-Diketones
Tirpak, Robin E.,Rathke, Michael W.
, p. 5099 - 5102 (2007/10/02)
Trimethylsilyl enol ethers of ketones are acylated by a variety of acid chlorides in the presence of zinc chloride or antimony trichloride.The major product of this reaction is the 1,3-diketone resulting from C-acylation.Some O-acylation is observed in most cases.Yields of 1,3-diketones varied but were usually good to excellent.
