Reacts with aldehydes and ketones to give O-methyloximes: J. Org. Chem., 27, 914 (1962); 28, 1523 (1963); Anal. Biochem., 22, 284 (1968). Open-chain aldoses have been prepared by ozonolysis of the methoximes of fully-acylated sugars: J. Org. Chem., 54, 4957 (1989). As with oximes, the lithiation of methoximes results in abstraction of a proton syn to the oxygen function (coordination stabilization): J. Org. Chem., 41, 439 (1976). For a review of the alkylation of carbonyl compounds via their nitrogen-containing derivatives, see: Synthesis, 517 (1983). In the presence of KO-t-Bu and a copper catalyst in DMF, aminates nitroarenes at the ortho (predominantly) and para positions: J. Org. Chem., 61, 442 (1996).
