Studies on the reduction and hydrolysis of nitroso acetals

Abstract

Chemical transformation of nitroso acetals derived from tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes have been investigated. New reduction methods were surveyed in an attempt to supplant the use of hydrogen and Raney nickel. Homogeneous catalytic hydrogenation was not successful, but samarium diiodide did effectively and selectively cleave one of the N—O bonds in a number of nitroso acetals. Acid-promoted hydrolysis of the nitroso acetals produced both α-alkoxy nitrones and hydroxamic acids selectively via expected pathways.Key words: nitroso acetals, hydroxamic acids, α-alkoxy nitrones, reduction, hydrolysis.