4848-85-5Relevant articles and documents
Phenyl Effects in Radical Additions to Alkenes
Giese, Bernd,Kretzschmar, Gerhard
, p. 3267 - 3270 (2007/10/02)
Reactions of cyclohexylmercuric salts 4 with NaBH4 in the presence of alkenes 8 yield products 10.The main step of the reaction sequence, the addition of a cyclohexyl radical (7) to alkene 8, can be measured using a competition technique.The data show that styrene reacts 30 - 40 times faster than expected by the ?p--value.This phenyl effect decreases in going from monosubstituted alkenes 8 to disubstituted alkenes 3, 2 and 1 because the steric hindrance of a coplanar orientation of the ?-system increases in the same order.