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The Reaction of Trihalgenomethyl Anions with Carbonyl Compounds: Competitive Reactivity Comparisons and Applications to the Synthesis of α-Trihalogenomethyl Alcohols

DOI: 10.1039/P29840001247

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1247 - 1252 (1984)

Update date:2022-07-30

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Authors:

Atkins, Paul J.Atkins, Paul J.

Gold, VictorGold, Victor

Wassef, Wasfy N.Wassef, Wasfy N.

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Article abstract of DOI:10.1039/P29840001247

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.

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