Premium
Reaction Model for the Formation of Benzene from Benzoates and Grignard Reagents
Author(s) -
Błaziak Kacper,
Miller Glenn B. S.,
Ryding Mauritz Johan,
Uggerud Einar
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700816
Subject(s) - chemistry , decarboxylation , benzoates , benzene , reagent , grignard reagent , hydrolysis , reaction mechanism , organic chemistry , computational chemistry , photochemistry , catalysis
Benzene formation from magnesium benzoate complexes in two steps (decarboxylation followed by hydrolysis) has been studied. Detailed reaction mechanisms are proposed based on evidence from tandem‐mass‐spectrometry experiments and bimolecular gas‐phase reactions, supported by extensive quantum‐chemical calculations. Formation of intermediate Grignard compounds by decarboxylation is seen to be the rate‐determining step of the overall process, but is essentially the same irrespective of the charge state (+1, 0, –1). The following reaction with H 2 O proceeds with a negative activation energy. The requirements for hydrolysis of metal benzoates to give benzene in aquaeous solutions are briefly discussed.