Zur Kenntniss der Aldehyde;

A Rationalization of Acid-Induced Reactions of Methylene-Bis-Amines, Methylene-Amines, and of Formaldehyde and Amines

“…Compounds formulated RNHCH2SO3Na or R2NCH2S03Na, viz., N-substituted aminomethane sulfonates, result (74) when I or la and formaldehyde react in presence of sodium bisulfite, or when preformed IV or III (which may be trimeric) is treated with sodium bisulfite (75)(76)(77)(78). They are the nitrogen-system counterparts of formaldehyde sodium bisulfite, which is known to be a sulfonate (79), as is acetaldehyde sodium bisulfite (80).…”

Catalytic Hydroamination of Unsaturated Carbon‐Carbon Bonds

“…They give experimental evidence that N-phenylethylideneamine is an intermediate, which evolves to an aldol-type condensation product (Scheme 4-9), known as an Ekstein-Eibner base [240][241][242]. PhNH-CH products CH 3 CH=NPh CH 2 =CHNHPh neat HgCl 2 (3.5%) PhNH 2 HC≡CH + Et 2 NH reacts with acetylene in the presence of copper(I) chloride or acetylide to give 3-diethylamino-1-butyne (Scheme 4-10) [243][244][245][246][247].…”

“…However, like N-phenylethylideneamine [239], N-alkylethylideneamines are not stable and undergo either aldol-type condensations to give Eckstein-Eibner bases [240][241][242] or condensation-elimination to give alkenylideneamines [252][253][254] as shown (Eq. 4.61) [250] or even higher vinylogs [250].…”

Azo Dyes

“…Amines, which tend to form diazoamino compounds, can easily be coupled at the para position if they have been reacted with formaldehyde and sodium hydrogen sulfite to form Nmethylenesulfonate [13]:…”