Synthesis and Reactivity of Chloromagnesium Dialkylaminoborohydride
Physical and Biological Sciences
CHEM 195A, B, and C
Like the words of a novel, a useful chemical is built up from small pieces attached and modified in a series of reactions. Industries like pharmaceuticals, polymers, pigments, and fuels rely on the vast library of well documented and studied organic chemical reactions to build their products. Carboxylic acid derivatives, linked by their common carbonyl substructure, are incredibly commonplace in medicines and plastics as well as in the chemistry of life. Oxidation and reduction, two tandem processes, represent a broad and useful type of reaction in organic chemistry. The interconversion reactions between carboxylic acid derivatives are useful transformations, and the oxidation and reduction of carboxylic acid derivatives comprise a large portion of these transformations. Chloromagnesium dimethylaminoborohydride (Me-MgAB) is a versatile and safe reagent capable of reducing many carboxylic acid derivatives to alcohols. Additionally, Me-MgAB has been shown to be capable of reducing tertiary amides—a common and easily accessible type of carboxylic acid derivative—to aldehydes, a useful but normally inaccessible functional group. Best of all, these reductions using Me-MgAB occur at room temperature—a rare and enticing ability in the organic chemistry laboratory and in the chemical industry.
