53226-58-7Relevant articles and documents
N-benzoyl-4-(dimethylamino)pyridinium chloride: Isolation and use for the direct benzoylation of alcohols
Wolfe, Michael S.
, p. 2975 - 2984 (1997)
A simple method for the formation and isolation of N-benzoyl-4- (dimethylamino)pyridinium chloride is described. This reagent can be employed directly for the benzoylation of secondary and tertiary alcohols.
Reduction of diesters of 1,2-diols. Regioselective C-O bond cleavage of the anionic forms
Macias-Ruvalcaba, Norma A.,Moy, Cheryl L.,Zheng, Zi-Rong,Evans, Dennis H.
, p. 4829 - 4834 (2007/10/03)
The electrochemical reduction of benzoate diesters of glycols has been studied in acetonitrile and N,N-dimethylformamide as solvents. The reductions occur in two closely spaced one-electron steps, and it was found that the dianion diradicals decompose by one of two routes, depending on the substituents on the ethylene moiety: cleavage of two benzoates to produce alkene or formation of benzil by way of a postulated cyclic intermediate to produce also the dianion of the diol. These correspond to cleavage of the R-OC(O)Ar bonds and the RO-C(O)Ar bonds, respectively. When the radical formed by the former cleavage is a primary or secondary radical, the reaction is too slow to compete with the latter reaction that produces benzil. However, when that radical is either tertiary or benzylic, the former cleavage reaction is fast and no benzil is detected. The dianions of p-cyano- and p-nitrobenzoate esters are rather stable on the voltammetric time scale. However, the addition of lithium ions results in detectable formation of 4,4′-dicyanobenzil from four different p-cyanobenzoate diesters.
Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds
Iwasaki, Fumiaki,Maki, Toshihide,Onomura, Osamu,Nakashima, Waka,Matsumura, Yoshihiro
, p. 996 - 1002 (2007/10/03)
A new facile method for monoacylation of diols has been developed. A variety of cyclic and acyclic diols, in particular 1,2-diols, were selectively monobenzoylated in good yields by the reaction with benzoyl chloride in the presence of a catalytic amount of dimethyltin dichloride and inorganic bases such as potassium carbonate. Furthermore, the method was successfully applied to a kinetic resolution of racemic 1-phenyl-1,2- ethanediol using a chiral organotin catalyst. The ee was dependent on the kind of base, water as an additive, and the reaction temperature.
