Rapid Ring‐Opening Metathesis Polymerization of Monomers Obtained from Biomass‐Derived Furfuryl Amines and Maleic Anhydride

Abstract

Figure 1. Structures of furan derivatives 1-5 and anhydrides 6-7.Scheme1.Prior work on ROMP of fully bio-based monomers prepared from itaconic anhydride.Scheme2.Synthesis of monomers 13 a-c.Scheme3.ROMP of monomers 13 a-c with Grubbs catalysts 9 and 14.

Application of the Intramolecular Diels–Alder Vinylarenе (IMDAV) Approach for the Synthesis of Thieno[2,3-f]isoindoles

“…Indeed, compound G can give the kinetically controlled IMDAF adduct H or the thermodynamically controlled IMDAV adduct I, depending on temperature. 4a Another paper 13 describes the isolation of the IMDAF product K through the cycloaddition of maleic anhydride to allylamine J. The data from this work provide the possibility of predicting that under heating isoindole K transforms into benzoisoindole L (not yet described).…”

“…Melting points for all crystalline compounds were measured on a capillary point apparatus Stuart SMP 10 or SMP 30 equipped with a digital thermometer and were uncorrected. 1 H, 13 C and 19 F NMR spectra were recorded at 300, 400, 500, 600 MHz (for 1 H), 75, 100, 125, 150 MHz (for 13 C) and 282 MHz (for 19 F) spectrometers, with TMS ( 1 H and 13 C NMR) or signal of CDCl 3 \DMSO-d 6 as the internal standards at 25 °C, unless otherwise noted. Data for 1 H NMR spectra are reported as follows: chemical shift  (ppm), referenced to TMS or CDCl 3 /DMSO-d 6 ; multiplicities using the standard abbreviations; coupling constants (Hz), and integration.…”

“…1 H NMR (600.2 MHz, CDCl 3 ):  = 7.17-7.14 (m, 2 H, H Ar ), 7.10 (d, J = 7.6 Hz, 1 H, H Ar ), 6.98 (dd, J = 3.3, 5.1 Hz, 1 H, 4-H Th ), 6.96 (br d, 130.2, 127.5, 127.3, 127.0, 125.7, 124.8, 124.3, 122.2, 117.4, 110.2, 46.0, 17.7. 13), 123 (100), 97 13), 91 (15, 79 (19), 77 (22), 65 (18), 45 (35).…”

“…8, 141.9, 129.3, 127.9, 127.5, 126.1, 125.8, 124.9, 124.3, 119.3, 117.6, 111.6, 46.0. (8,35 Cl), 214 (5), 123 (100), 97 (10), 79 (13), 77 (11), 45 (29).…”

“…C NMR (150.9 MHz, CDCl 3 ):  = 148.0, 143.0, 141.5, 134.3, 129.4, 129.0, 127.6, 126.9, 126.8, 125.7, 124.8, 123.4, 117.8, 113.1, 46.1. 10, 212 (26), 184 (12), 152 (10), 115 (13), 77 (30), 51 (14).…”