The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Free radical and anionic polymerization of some N-substituted maleimides》. Authors are Cubbon, R. C. P..The article about the compound:1-(tert-Butyl)-1H-pyrrole-2,5-dionecas:4144-22-3,SMILESS:O=C(C=C1)N(C(C)(C)C)C1=O).Synthetic Route of C8H11NO2. Through the article, more information about this compound (cas:4144-22-3) is conveyed.
N-Substituted maleimide monomers were prepared and polymerized by free-radical and anionic initiation. N-Alkylmaleimides were prepared by reaction of the primary amines with maleic anhydride in xylene, drying over anhydrous Na2SO4, and redistg. under reduced N pressure. The N-Et derivative m. 45.5°, b18 86°; the N-iso-Pr derivative m. 20°, b10 75° the N-Bu derivative m. 20°, b20103° the N-iso-Bu derivative m. 42.5; the N-tert-Bu derivative b18 104°; the N-n-octyl derivative b18 37.5°, the N-benzyl derivative b18 50°, b5 120°. The N-Et derivative was recrystallized from C6H6 and the N-iso-Bu derivative from aqueous alc. The N-Ph derivative was prepared by the ring closure of N-phenylmaleamic acid with Ac2O and NaOAc, and was recrystallized from H2O. For free radical polymerization, monomer and C6H6 were introduced into a Carius tube with 0.02-0.05% by weight of azodiisobutyronitrile, the tube was sealed under O-free N, was kept at 100° for 5-15 hrs., and the polymers were recovered by precipitating into MeOH, yields 70-80%, inherent viscosities in 0.5% HCONMe2 0.3-0.8. K2S2O8-NaHSO3 initiation gave higher yields, but polymers with lower viscosities. The polymers had penetrometer softening points of 110-330°. X-ray powder photographs showed 2 marked interplanar spacings. The polymers could not be drawn. Anionic polymerization took place in toluene and tetrahydrofuran with a pentane/heptane solution containing 0.01-0.02 mole/l. of BuLi initiator. The dry solvent was distilled into a vessel equipped with a vacuum-sealed stirrer, N inlet and outlet, and a rubber serum cap. The monomer, 0.27 mole/l., was introduced, the vessel was cooled to 0 to 70°, and the initiator solution was injected. Polymerization was terminated after 20-180 min. by MeOH and the deep-red color, owing to the reaction of base with residual unsaturation, was destroyed with dilute HCl, yield in toluene 20-2%, inherent viscosity 0.115-0.172. Yields were 90-5% in tetrahydrofuran. Poly(N-ethylmaleimide) and poly(N-butylmaleimide) were cross-linked. X-ray studies indicated that both types of initiation produced polymers with predominantly threo-diisotactic configuration.
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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics