87142-97-0Relevant academic research and scientific papers
Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System
Cheng, Zhao,Guo, Hongmei,Huang, Guozheng,Rexit, Abulikemu Abudu,Wang, Hui,Zheng, Meng-Xia
supporting information, p. 6455 - 6458 (2020/10/21)
A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.
The Reaction of Polyhalogenomethanes with Aldehydes and with 1,3,5-Trinitrobenzene in the Presence of Tin(II) Salts: Evidence for the Formation of Trihalogenomethyl Anions
Atkins, Paul J.,Gold, Victor,Routledge, Paul J.
, p. 1563 - 1566 (2007/10/02)
The (previously reported) formation of 2,2,2-tribromoethanols by the reaction of aromatic aldehydes with tetrabromomethane in the presence of tin(II) fluoride in dimethyl sulphoxide solution also occurs when tin(II) chloride is used in place of the fluoride.Analogous reactions occur with certain other tetrahalogenomethanes, but not with trihalogenomethanes nor with fluorine-containing tetrahalogenomethanes.When the aldehyde is replaced by 1,3,5-trinitrobenzene, Meisenheimer adducts derived from trihalogenomethyl anions are formed.The trihalogenomethyl anions are thought to be a product of the two-electron reduction of tetrahalogenomethanes by tin (II).
The Reaction of Trihalgenomethyl Anions with Carbonyl Compounds: Competitive Reactivity Comparisons and Applications to the Synthesis of α-Trihalogenomethyl Alcohols
Atkins, Paul J.,Gold, Victor,Wassef, Wasfy N.
, p. 1247 - 1252 (2007/10/02)
Trihalogenomethyl anions, generated by decarboxilation of trichloro- and tribromo-acetic acid in dimethyl sulphoxide solution, react with added aldehydes.In the presence of 1,3,5-trinitrobenzene, the reaction with aldehydes competes with the formation of the coloured Meisenheimer adduct.The reduction in absorbance from the value in the absence of aldehyde has been used tomeasure the reactivity of trihlogenomethyl anions towards a series of aldehydes relative to their reactivity towards trinitrobenzene.For 4-substituted benzaldehydes, the reactivities obey a linear p?- relationship.The most reactive aldehyde used is only two times less reactive towards CCl3(1-) or CBr3(1-) than hydrogen ions, and it is concluded that, in dimethyl sulphoxide solutions, the reaction between trichloromethyl anions and hydrogen ions is not encounter-controlled.The reactions with aldehydes have been used to prepare several new compounds of the formula RCH(OY)CX3 where R = aryl or pyridyl, X = Br or Cl, and Y = H or COCH3.
The Decomposition of Trihalogenoacetic Acids in Dimethyl Sulphoxide: a Mild Route from Carbonyl Compounds to Trihalogenomethylethanols and Trihalogenomethyl Ketones
Atkins, Paul J.,Gold, Victor,Wassef, Wasfy N.
, p. 283 - 284 (2007/10/02)
Solutions of trichloro- and tribromo-acetic acid in dimethyl sulphoxide in the presence of carbonyl compounds react at room temperature to give isolable products corresponding to the addition of H-CX3 across the carbonyl double bond.
