Erowid References Database
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Gilsdorf RT, Nord FF.
“Reverse Addition of Lithium Aluminum Hydride to Nitroolefins”.
The Department of Organic Chemistry and Enzymology. 1952 Apr 5;? (247):1837-43.
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Abstract
The reverse addition of lithium aluminum hydride to I-phenyl-2-nitropropene-1 was studied in detail in order to correlate this method with those previously recorded in the literature for the reduction of nitroolefins. A variety of products was isolated by varying the reaction temperature and the ratio of reactants. Among them was l-phenyl-2-nitropropane, rising from the selective reduction of the double bond. By employing acidic hydrolysis of the intermediate organometallic complex, phenylacetone was obtained via a modified Nef reaction. A study on the reverse addition of lithiium aluminum hydride to w-nitrostyrene, led to the development of a novel method of converting benzaldehyde to its next higher homolog.
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