Lithium Aluminum Hydride Reduction Studies of Rigid $\alpha$-Oximino Ketones

Lithium Aluminum Hydride Reduction Studies of Rigid $\alpha$-Oximino Ketones

Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.