Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride
Well-controlled and extremely rapid ring-opening metathesis polymerization of unusual oxanorbornene lactam esters by Grubbs third-generation catalyst is used to prepare a range of bio-based homo- and copolymers. Bio-derived oxanorbornene lactam monomers were prepared at room temperature from maleic anhydride and secondary furfuryl amines by using a 100 % atom economical, tandem Diels–Alder lactamization reaction, followed by esterification. Several of the resulting homo- and copolymers show good control over polymer molecular weight and have narrow molecular weight distributions.
Blanpain, Anna,Clark, James H.,Farmer, Thomas J.,Guo, Yuanlong,Ingram, Ian D. V.,Kendrick, John E.,Lawrenson, Stefan B.,North, Michael,Rodgers, George,Whitwood, Adrian C.
Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives
The regio- and stereoselectivity of the [4+2] cycloaddition of maleic, citraconic, dichloromaleic, and dibromomaleic anhydrides to difurfuryl amines and secondary furfurylamines were studied. N-Furfuryl-, N-phenyl-, and N-benzylhexahydrooxoepoxyisoindole-7-carboxylic acids were synthesized. An approach was developed for obtaining hexahydroepoxyoxoisoindole-7-carboxylic acid unsubstituted at the nitrogen atom. Aromatization of the oxabicycloheptene fragment of the dihaloepoxyiso-indolonecarboxylic acids gave a series of 7-carboxy-2-R-isoindol-1-ones.
Preparative synthesis of 7-carboxy-2-R-isoindol-1-ones
A preparative method for the synthesis of 7-carboxy-2-R-isoindol-1-ones was developed on the basis of the [4+2] cycloaddition of secondary furfurylamines to maleic anhydride.