2638-22-4Relevant academic research and scientific papers
A Cheap, Simple and Efficient Method for the Preparation of Symmetrical Carboxylic Acid Anhydrides
Kazemi, Foad,Sharghi, Hashem,Nasseri, Mohammad Ali
, p. 205 - 207 (2004)
A manipulatively simple and facile one-pot procedure for the synthesis of symmetrical anhydride is reported. Treatment of carboxylic acids with tosyl chloride in K2CO3 media under solvent free conditions gives the corresponding anhydrides in good to excellent yields in a short reaction time via carboxylic sulfonic anhydride as the key intermediate.
Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols
Mayr, Stefanie,Marin-Luna, Marta,Zipse, Hendrik
, p. 3456 - 3489 (2021/03/01)
Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.
