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New Dicarboxylic Acid Anhydride for Ambient‐Temperature Castagnoli‐Cushman Reactions
Author(s) -
Chizhova Maria,
Bakulina Olga,
Dar'in Dmitry,
Krasavin Mikhail
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601207
Subject(s) - glutaric acid , diastereomer , imine , chemistry , organic chemistry , acid anhydride , polymer chemistry , dicarboxylic acid , characterization (materials science) , catalysis , materials science , epoxy , nanotechnology
Abstract A novel 3‐phenyl‐4‐thiaglutaric anhydride was employed as a highly reactive partner for the Castagnoli‐Cushman reaction. This, in combination with the use of DMF as a reaction medium, resulted in a drastic lowering of the reaction temperature to ambient (compared to the 110–150 °C range typical for similar processes involving glutaric anhydride) and an extended reaction scope (with respect to substitution pattern in the imine component). Diastereomeric products were separated, in the form of respective methyl esters, and their comparative NMR characterization led to preliminary generalizations regarding the syn‐ and anti‐ series.