75089-67-7Relevant academic research and scientific papers
A Mechanism for the Photosubstitution of Fluoro- and Methoxy-benzenes by Diethylamine
Bunce, Nigel J.,Cater, Stephen R.
, p. 169 - 174 (2007/10/02)
The photochemical reactions of fluoro- and methoxy-benzenes with diethylamine produce addition and substitution products.The proposed mechanism involves quenching of the singlet state by the amine to give an exciplex.Proton transfer within the exciplex leads to the amine adducts, some of which can undergo elimination to yield the substitution products.
Exited State Substitution and Addition Reactions of Aryl Fluorides with Aliphatic Amines
Gilbert, Andrew,Krestonosich, Stefan
, p. 1393 - 1399 (2007/10/02)
Fluorobenzene and the difluorobenzenes undergo photochemical reaction with t-butylamine and diethylamine to give both 1:1 adducts and substitution products but only the latter are formed from hexafluorobenzene and diethylamine.Both cine and 'normal' substitution products are observed from the difluoro-compounds and the mechanism to account for this is considered to involve a polar excited-state complex between the addends and an addition-elimination process rather than benzyne intermediates. 1,2-Acyclic amine photoadducts are produced from most systems but the corresponding 1,4-isomers are the major adducts from p-difluorobenzene and that from diethylamine is unique in undergoing thermal retro-addition to the starting materials rather than conversion into the aniline derivative.
