90265-27-3Relevant academic research and scientific papers
Radical Chain Reactions with Maleic Anhydrides - Contrathermodynamic Stereoselectivity
Giese, Bernd,Kretzschmar, Gerhard
, p. 3175 - 3182 (2007/10/02)
The reactions of cyclohexylmercuric chloride with NaBH4 and alkenes 1a-g yield 60-84percent of products 3, 4 and 6 in a radical chain process (table 1).Caused by steric effects of substituents Z at least 97percent of the radical attack occurs at the unsubstituted carbon atom of maleic anhydrides 1c-g.Only fluoromaleic anhydride 1b is attacked by cyclohexyl radicals predominantly at the substituted carbon atom, because fluorine is a tiny, electron releasing substituent.Radicals 2 are trapped predominantly from the anti-direction by the H-donor (figure 1), yielding cis-compounds 3as main products.This "contrathermodynamic" stereoselectivity ranges between 2.3 and 19 (table 1).
