Cellulose‐Derived Functional Polyacetal by Cationic Ring‐Opening Polymerization of Levoglucosenyl Methyl Ether

Abstract

The unsaturated bicyclic acetal levoglucosenyl methyl ether was readily obtained from sustainable feedstock (cellulose) and polymerizedb yc ationic ring-opening polymerization to produce as emicrystalline thermoplastic unsaturated polyacetal with relatively high apparent molar mass (up to ca. 36 kg mol À1 )a nd decent dispersity (ca. 1.4). The double bonds along the chain can undergo hydrogenation and thiolene reactions as well as crosslinking,t hus making this polyacetal potentially interesting as ar eactive functional material.Supportinginformation (including experimental details and characterization data) and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

“…The 1 H NMR spectrum of the hydrogenated product showed no signals at 6.11–5.92 ppm and 5.93–5.83 ppm, but the appearance of new signals at ca. 1.45–2.00 ppm [ 46 , 48 ].…”

“…We suggest that the solvent reacts with methyl triflate to form triflic acid and methylated DLG ( Figure 5a ). The strong acid triflic acid then can initate the polymerization with a proton [ 46 ]. Alternatively, the triflic acid could react potentially together with DLG with a monomer, leading to a DLG-initiated polymer chain ( Figure 5b ).…”

“…Dihydrolevoglucosenone (DLG) is prepared by hydrogenation of levoglucosenone in the presence of palladium as a catalyst. Recently, Debsharma et al reported the CROP of levoglucosenyl alkyl ether in CH 2 Cl 2 at 0 °C and at room temperature using triflic acid or boron trifluoride etherate as initiators [46][47][48]. The 1 H NMR spectra of the resulting polymers showed significant signals at 6.11-5.92 ppm, 5.93-5.83 ppm, 4.36-4.27 ppm, and 3.92-3.82 ppm.…”

Stereoregular functionalized polysaccharidesviacationic ring-opening polymerization of biomass-derived levoglucosan

“…[20][21][22][23][24] In addition, stereoselective cROP of levoglucosan to obtain polysaccharides with 1,6-a-glycosidic linkages is attractive from a sustainability standpoint since these linkages have demonstrated susceptibility to enzymatic and acidic hydrolysis. [25][26][27] Despite these advantages, levoglucosan has received considerably less attention in the sustainable polymers eld as compared to levoglucosenone, [28][29][30][31][32][33][34][35][36][37] another anhydrosugar than can be obtained in small quantities from cellulose pyrolysis. 13 The cROP of protected levoglucosan derivatives was rst reported more than 50 years ago, however the synthetic routes employed had some major drawbacks.…”

Three-Component Asymmetric Polymerization toward Chiral Polymer

“…Direct polymerization of enantioenriched monomers and asymmetric kinetic resolution polymerization (AKRP) of racemic monomers are two commonly used methods for constructing chiral polymers. [14][15][16][17][18][19][20][21][22] However, neither of them could efficiently afford chiral poly-triazolyl-methanamines due to the above-mentioned issues.…”