126550-94-5Relevant academic research and scientific papers
Simple diastereoselectivity on addition of α-haloalkyl grignard reagents to benzaldehyde
Schulze, Volker,Nell, Peter G.,Burton, Andrew,Hoffmann, Reinhard W.
, p. 4546 - 4548 (2003)
The addition of α-haloalkyl Grignard reagents to benzaldehyde occurs with simple diastereoselectivity substantially higher than that of the corresponding lithium reagents. Reaction in the presence of dimethyl-aluminum chloride suppresses subsequent Oppenauer oxidation of the resulting Mg-alkoxides by excess benzaldehyde.
Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals
Cao, Yuanjie,Chen, Tieqiao,Huang, Tianzeng,Liu, Long
, p. 8697 - 8701 (2020/06/08)
A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.
α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones
Gallo, Rafael D. C.,Ahmad, Anees,Metzker, Gustavo,Burtoloso, Antonio C. B.
, p. 16980 - 16984 (2017/11/27)
A one-pot alkylation–halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem-difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem-dihalogenated ketones containing a combination of the same or two different halogens. Kinetic isotopic effects as well as reaction kinetic experiments give insight to the mechanism of these reactions.
Oxidative iodination of carbonyl compounds using ammonium iodide and oxone
Marri, Mahender Reddy,MacHarla, Arun Kumar,Peraka, Swamy,Nama, Narender
supporting information; experimental part, p. 6554 - 6559 (2012/01/02)
A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.
An expedient protocol for conversion of olefins to α-bromo/iodoketones using IBX and NBS/NIS
Moorthy, Jarugu Narasimha,Senapati, Kalyan,Singhal, Nidhi
experimental part, p. 2493 - 2496 (2009/08/17)
A variety of olefins have been shown to undergo conversion to the corresponding α-bromo/iodoketones when reacted with NBS/NIS and IBX in DMSO at room temperature. While the reaction is found to occur rapidly with e-rich arylolefins leading to the corresponding haloketones in 65-95% yields in 0.3-3.0 h, those containing e-withdrawing groups are found to yield diketones concomitantly, such that the latter are the exclusive products over extended duration of the reactions.
Discrimination of enantiotopic iodine atoms by an iodine/magnesium exchange reaction
Schulze, Volker,Hoffmann, Reinhard W.
, p. 337 - 344 (2007/10/03)
An enantioselective iodine/magnesium exchange reaction between the diiodoalkane 4 and a chiral Grignard reagent 12 has been realized at -78°C in THF. The resulting α-iodoalkylmagnesium reagents 13 are configurationally stable under these conditions and during trapping by a benzaldehyde/dimethylaluminium chloride system to furnish the iodohydrins 19 and epoxides 9.
Substituent Effects in 13C-N.M.R. Spectra of Diastereomeric Chalcone Dihalogenides. VIII. Investigations of α- and β-Halogene Dihydrochalcones and Calculation of 13C-chemical Shifts of Diastereomeric Chalcone Dihalogenides and Chalcone Halogenohydrins
Weber, F. G.,Radeglia, R.
, p. 212 - 222 (2007/10/02)
The chemical shifts of C-α and C-β in the 13C-n.m.r. spectra are determined and compared with calculated values from an incremental system and Taft relationship.The correlations are extended for erythro and threo isomers of halohydrins and diastereomeric
