Reactions of hydroxyalkyl esters with phenyl isocyanate

Abstract

ABSTRACT:In a reaction between 2-hydroxyethyl methacrylate and phenyl isocyanate (PI), we did not obtain the expected urethane ester monomer but products of its subsequent conversion, namely, ethylene dimethacrylate and ethylene bis(phenylcarbamate). The effects of the structures of various hydroxyalkyl esters on the transformation of the products of their reaction with PI into their respective diesters and alkanediyl bis(phenylcarbamates) were observed with standard spectral methods (IR, 1 H-NMR) and chromatographic and classical separation techniques.

Facile oxidative hydrolysis of acetals to esters using hypervalent iodine(III)/LiBr combination in water

“…Furthermore, cyclic acetals derived from aliphatic aldehydes generally afforded the corresponding esters in good yields (entries [13][14][15][16][17][18][19][20][21][22]. High yields were also obtained with the cyclic acetals derived from a-disubstituted aldehydes (entries [23][24][25][26]. Finally, the oxidative hydrolysis of acyclic dialkyl acetals 4a and 4b proceeded readily, affording the corresponding simple esters 5a and 5b in moderate yields (entries 27 and 28).…”

“…Column chromatography was carried out using silica gel 60 (0.063-0.200 mm). Known compounds were characterized by 1 H and 13 C NMR, IR, and mass spectroscopy, and their spectroscopic data were identical to those previously reported in the literature; (2a), 24 (2b, 2e, 2g-2j, 2m, 2n, 2s-2v, 2y, 2z, 5b), 20 (2c), 25 (2f), 7b (2k), 9c,16b (2l), 16b (2w), 25 (5a). 26 All new compounds were characterized by 1 H and 13 C NMR, IR, and high-resolution mass spectroscopy.…”

Synthesis of polyetherols with isocyanuric ring. Kinetics and mechanisms of reactions, part 1: Reaction between isocyanuric acid and ethylene carbonate

“…Incorporation of aromatic rings with nitrogen atoms into the polymer can induce its thermal stability 1. Polyetherols with an isocyanuric ring are useful for obtaining thermally resistant polyurethane foams 2.…”

“…The process can be performed in DMSO, the best solvent for IA, in the presence of basic catalysts such as triethylamine or tetralkylammonium hydroxides. This high‐boiling solvent must be then distilled off, which results in partial decomposition of the product, which becomes contaminated with products of side reactions 1. Furthermore, oxirane substrates are toxic, flammable, and explosive.…”

“…The latter are nonflammable and environmentally friendly 7. It should be emphasized that the products of the reaction of imide groups and oxiranes or carbonates are the same, according to the following scheme 1: …”