Reactivity of the carbonyl group in water. Generation of azomethine ylides from aqueous formaldehyde: Michael addition versus dipolar trapping
Abstract
The ability of aqueous formaldehyde to generate azomethine ylides has been studied. Treatment of methyl N-methylglycinate with dipolarophiles in commercial aqueous formaldehyde gives pyrrolidines by azomethine ylide cycloaddition which competes with a Michael addition.