A New Method for the Cleavage of Nitrobenzyl Amides and Ethers.

A mild and efficient o- and p-nitrobenzyl cleavage protocol was developed. o- and p-Nitrobenzyl groups were easily removed from a variety of substrates using 20% aqueous NaOH in methanol at 75 °C, presumably via oxidation at the benzylic position by oxygen dissolved in the solution. These easily introducible and removable nitrobenzyl groups can serve as valuable protecting groups for the synthesis of multifunctional, complex molecules.