The formation of isopropylidene acetals of erythritol and ribitol under conditions of kinetic control

Sugar-Derived Cyclic Acetals as Comonomers for Cationic Copolymerization with Vinyl Ethers

“…Most of the sugar-derived cyclic acetals used in this study (M-1, M-4, X-1, X-2, X-3, X-4, E-1, E-2, S-1, G-1, and T-1 in Scheme D) were synthesized by one-step reactions from sugar, sugar alcohols, aldonic acid, or aldaric acid according to the literature methods ,,− (see the Experimental Section in the Supporting Information). The one-step synthesis of the monomers is an advantage of this study.…”

“…Detailed comparisons of the M-4, S-1, and G-1 results are discussed later. E-1 and E-2, − which were obtained from meso -erythritol and have two five-membered rings, underwent copolymerizations with CEVE to yield copolymers with unimodal MWDs (entries 7 and 8; Figure ; see Figure S4 for the 1 H NMR spectrum of the product from E-2) . In the cases of X-1, X-2, X-3, and X-4, − which were derived from d -(+)-xylose and have five- and six-membered cyclic acetal moieties, the substituents at the carbons adjacent to two oxygen atoms were responsible for the copolymerizations.…”

“…Motivated by promising possibilities of sugars for polymer synthesis, we focused on sugar-derived cyclic acetals as monomers for ROP. Since early 1900s, various cyclic acetals were synthesized by condensation reactions of sugars and carbonyl compounds such as aldehydes and ketones. − Some sugar-derived cyclic acetals bearing hydroxy groups were used as monomers in polycondensation, yielding polymers with rigid cyclic structures in the main chains . However, as far as we know, there have been no example that demonstrate ROP of sugar-derived cyclic acetals except for anhydrosugars.…”

“…In this study, we investigated copolymerizations of VEs and sugar-derived cyclic acetals synthesized by condensations reactions of carbonyl compounds with sugar, sugar alcohols, aldonic acid, or aldaric acid, such as mannitol, xylose, erythritol, sorbitol, gluconic acid, and tartaric acid (Scheme D). − The synthesized monomers have two or three cyclic acetal moieties of five-, six-, or seven-membered rings in an independent or fused manner. As a result of systematic investigation on cationic polymerizations with 2-chloroethyl VE (CEVE; Scheme C), polymerizabilities of the cyclic acetals were demonstrated to differ depending on bulkiness, stereo configuration, and substituents.…”

A comparison of homogeneous and heterogeneous Brønsted acid catalysts in the reactions of meso-erythritol with aldehyde/ketones

“…2 [33,34]. The products were identified by comparison with published 1 H and 13 C NMR data [35][36][37][38][39]. [33,34] A representative 1 H NMR spectrum of the bis-ketal (3b), ketal-ether (4b) product mixture from the Amberlite-15 catalyzed reaction of meso-erythritol (1), with acetone (2b) is shown in Fig.…”