Kharasch addition
From Infogalactic: the planetary knowledge core
The Kharasch addition is an organic reaction and a metal-catalysed free radical addition of CXCl3 compounds (X = Cl, Br, H) to alkenes.[1] The reaction was discovered by Morris S. Kharasch in the 1940s.[2][3][4]
The basic reaction scheme runs as follows:
- R2C=CH2 + R'X → R2CX-CH2R':
and proceeds through the CXCl2 free radical. Examples of organohalides are carbon tetrachloride and chloroform. The addition is an anti-Markovnikov addition. Early work linked the addition to olefin polymerization [5] and is therefore considered a first step into what was to become atom transfer radical polymerization.
An example of Karasch addition is the synthesis of 1,1,3-trichloro-n-nonane from 1-octene, chloroform and ferric chloride.[6]
References
- ↑ Name reactions: a collection of detailed reaction mechanisms, Jie Jack Li Springer; 2nd edition (September 17, 2003) 3540402039
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- ↑ Organic Syntheses, Coll. Vol. 5, p.1076 (1973); Vol. 45, p.104 (1965). link
