123807-35-2Relevant academic research and scientific papers
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.
STUDIES ON THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS. IX. SEPARATION OF DIASTEREOMERIC DIOL COMPOUNDS
Anchisi, Carlo,Maccioni, Antonio,Maccioni, Anna Maria,Podda, Gianni
, p. 73 - 76 (2007/10/02)
The separation of diastereomeric diols by transformation into the corresponding dioxastannolanes was carried out.The products are solid, stable and easily separable by fractional crystallization.By reaction of acids (or acyl halides) with the stannolanes the corresponding diols (or esters) were obtained in a high degree of purity.The structures of the compounds prepared were assigned on the basis of their analytical, physical and spectral data.
