The Journal of Organic Chemistry

. alpha.-Iodination of some aliphatic acids. Substituent effect and optimum conditions

Y Ogata, S Watanabe

Index: Ogata, Yoshiro; Watanabe, Shinya Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2831 - 2834

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Citation Number: 12

Abstract

The chlorosulfonic acid promoted a-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 m view of Taft's equation: log krel= p, CE,+ SEE,, where po=-1.20 and 6= 1.55 at 80 “C. The transition state is discussed, which involves the electrophilic addition of I2 to a ketene intermediate. Aliphatic acids with less steric ...

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