Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to alpha,beta-unsaturated carboxylates
Abbreviated Journal Title
J. Fluor. Chem.
dehydrobromination; hydrolysis; halomethane; Chemistry, Inorganic & Nuclear; Chemistry, Organic
Alternative mechanisms for the title reactions are probed. The previously-reported pathway involving double dehydrobromination to a difluorodiene is operative in at least one case, but this route is specifically excluded for systems that cannot dehydrobrominate to dienes yet still yield carboxylates upon alkaline hydrolysis. Although S(N)2, S(N)1, S(RN)1, and monoelimination-addition processes appear formally possible, an S(N)2' mechanism is implicated by studies on model compounds. (C) 2000 Elsevier Science S.A. All rights reserved.
Journal of Fluorine Chemistry
"Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to alpha,beta-unsaturated carboxylates" (2000). Faculty Bibliography 2000s. 2517.