65164-70-7Relevant articles and documents
α-Iodination of Some Aliphatic Acids. Substituent Effect and Optimum Conditions
Ogata, Yoshiro,Watanabe, Shinya
, p. 2831 - 2834 (2007/10/02)
The chlorosulfonic acid promoted α-iodination of some aliphatic acids in 1,2-dichloroethane has been studied.In contrast to the bromination, the effect of substituents on the rate shows not only a polar effect but also a steric effect in view of Taft's equation: , where ρ? = -1.20 and δ = 1.55 at 80 deg C.The transition state is discussed, which involves the electrophilic addition of I2 to a ketene intermediate.Aliphatic acids with less steric hindrance at the α-position, except acetic acid, are α-iodinated in good yields (ca. 80-100percent).The optimumconditions for α-iodination of long-chain aliphatic acids with caprylic acid as a model substrate are described.