HETEROAROMATIC PRIMARY AMINES AND FORMALDEHYDE - THE FORMATION OF N-HYDROXYMETHYL DERIVATIVES

A product study of the reaction of three heteroaromatic primary amines with paraformaldehyde was made: N-hydroxymethylamines were identified in all cases. Two of them yielded also N,N-dihydroxymethyl derivative s. X-Ray diffraction structure determination on one of the N-hydroxyme thyl derivatives ruled out the presence of internal hydrogen bonding i n the solid state, notwithstanding the almost ideally planar arrangeme nt of the aromatic moiety and the amino function.