The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of cyclic Poly(methyl methacrylate) via N-Heterocyclic carbene (NHC) initiated-anionic polymerization and subsequent ring-closing without need of highly dilute conditions》. Authors are Oga, Yosuke; Hosoi, Yuhei; Takasu, Akinori.The article about the compound:1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidenecas:141556-42-5,SMILESS:CC1=CC(C)=CC(C)=C1[N+]2=[C-]N(C3=C(C)C=C(C)C=C3C)C=C2).Category: indole-building-block. Through the article, more information about this compound (cas:141556-42-5) is conveyed.
A cyclic polymethacrylate was prepared via the anionic polymerization of Me methacrylate (MMA) initiated by a 1:1 adductof Me sorbate (MS) and a N-heterocyclic carbene (NHC) without the need for highly dilute conditions, because an α-terminal imidazolimium group is neighboring to the propagating anion during the polymerization The polymerization proceeded quant. using methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) as the Lewis acid to give the poly(MMA) with the MS unit in the α-terminus, and an Mn of 7.2 × 103-29.1 × 103 with a mol. weight distribution (Mw/Mn = 1.16-1.56). From proton (1H) NMR and matrix assisted laser desorption/ionization (MALDI-TOF) mass spectra, coupled with size exclusion chromatog. (SEC) of the poly (MMA) produced before and after ozonolysis of the internal carbon-carbon double bond in the MS unit, we found that ring-closing reaction was induced by nucleophilic substitution of the propagating anion to the neighboring carbon of the α-terminal carbenyl (imidazolimium) group to synthesize cyclic poly (MMA) following complete the monomer consumption.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles