92617-56-6Relevant articles and documents
Reductive Addition of Polyhalomethanes and Their Related Compounds to Aldehydes and 1,2-Elimination of the Coupling Products in a Pb/Al Bimetal Redox System
Tanaka, Hideo,Yamashita, Shiro,Yamanoue, Motoi,Torii, Sigeru
, p. 444 - 450 (2007/10/02)
A Pb/Al bimetal system was used to carry out reductive addition of tetrachloromethane, tetrabromomethane, bromotrichloromethane, trichloroacetamide, and trichloroacetonitrile to aldehydes.Subsequent 1,2-elimination of the halogen atom and hydroxyl group from the coupling products was also performed with the Pb/Al bimetal system.The technology was successfully applied to stereocontrolled syntheses of ethyl trans- and cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates.
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.
