2-Chloroethyl vinyl ether → 2-Vinyloxyethyl phthalimide

Participants

Reaction Conditions

Reaction Steps

Amine-containing enol ether copolymers (i.e. Poly(alkyl enolether-co-vinyloxy ethylamine) Polymers: 2-(vinyloxy)ethyl phthalimide (ImVE) was prepared by reacting 2-chloroethyl vinyl ether (25 g, 0.24 mol) with potassium phthalimide (25 g, 0.135 mol) in dimethyl foramide (75 mL) using tetra-n-butyl ammonium bromide as a phase transfer catalyst. This reaction mixture was stirred at 100° C. for 6 h then poured into 800 mL distilled water, and filtered and washed with a large amount of distilled water. The recovered yellowish crystals where then recrystallized twice from methanol to give white crystals, which were then dried for 48 h under reduced pressure. Polymerization was carried out in anhydrous methylene chloride at −78° C. under a blanket of dry nitrogen gas in oven-dried glassware. The reaction was initiated by adding borontrifluoride diethyl etherate to ImVE, and a mixture of enol ethers. The reaction was allowed to run for 3 h at −78° C., and then allowed to warm for ten minutes at RT, and then quenched with prechilled ammonia saturated methanol. The product was then evaporated to dryness under reduced pressure to give the product polymers. The polymer was then dissolved in a 1,4-dioxane(2)/methanol mixture and 10 equivalents (eq.) of hydrazine hydrate per mole of amine present. This solution was then refluxed for 2 h, cooled to RT, and the solvent was then removed under reduced pressure. This solution was then brought up in 0.5M HCl, and refluxed for 60-minutes. The cooled solution was then transferred to 3,000 MW dialysis tubing and dialyzed (4×5 L) for 48 h. This solution was then frozen and lyophilized. The following polymers were generated using this procedure:

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