Synthesis, Characterization, and Selectivity of Bifunctional Couplers

Bifunctional couplers based on carbonate chemistry - Series A, B, and C - that are able to combine molecules bearing amine groups via substitution and addition reaction (Series A) or only via addition (Series B and C) were synthesized and characterized. The reactivity and selectivity of the two functional groups of couplers toward primary amines in different conditions were studied. The reactivity of couplers of Series B towards secondary and tertiary amines was investigated. The effect of adjacent groups (alpha/delta-position to O/N sides of urethane groups or alpha-position to ether groups) on the reactivity of the five-membered cyclic carbonates was studied using model compounds 4, 5, 13, and 16.