35951-33-8Relevant academic research and scientific papers
REGIOSELECTIVE REPLACEMENT OF THE HYDROXY GROUP IN ALCOHOLS BY MEANS OF TRIHALOACETIC DERIVATIVES IN PRESENCE OF TRIPHENYLPHOSPHINE
Matveeva, E. D.,Yalovskaya, A. I.,Cherepanov, I. A.,Bundel', Yu. G.,Kurts, A. L.
, p. 1409 - 1415 (2007/10/02)
The investigation of the reactions of trichloroacetonitrile with 2-decanol, 2-methyl-3-octanol, 2,4-dimethyl-3-pentanol, and 2,2-dimethyl-1-propanol in presence of triphenylphosphine shows that the formation of alkyl chlorides from the corresponding alcohols goes regiospecifically: Even for 2,4-dimethyl-3-pentanol the amount of the isomeric chloride does not exceed 1percent, while neopentyl alcohol is converted into neopentyl chloride in 95percent yield.On the introduction of "external" nucleophiles (iodide and thiocyanate ions) into the reaction mixture the predominating reaction product is the alkyl chloride.As a result of the reaction of bromotrichloromethane with 1-nonanol and triphenylphosphine a mixture of the alkyl chloride and the alkyl bromide is formed.
