Diels-Alder Cycloaddition of 2,5-Bis(hydroxymethyl)furan (BHMF) and N-Phenylmaleimide Derivatives
Issued Date
2024-01-01
Resource Type
eISSN
24701343
Scopus ID
2-s2.0-85201431459
Journal Title
ACS Omega
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SCOPUS
Bibliographic Citation
ACS Omega (2024)
Suggested Citation
Shukla H., Promcharoen P., Poonsawat T., Chakarawet K., Chumkaeo P., Somsook E. Diels-Alder Cycloaddition of 2,5-Bis(hydroxymethyl)furan (BHMF) and N-Phenylmaleimide Derivatives. ACS Omega (2024). doi:10.1021/acsomega.4c03804 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/100602
Title
Diels-Alder Cycloaddition of 2,5-Bis(hydroxymethyl)furan (BHMF) and N-Phenylmaleimide Derivatives
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Abstract
Currently, amidst atmospheric menace where natural calamities such as wildfire and floods are becoming more frequent than ever, biobased derivatives offer a sustainable alternative to conventional ways, for instance, petrochemical commodities. Biobased products, obtained from agricultural waste, including 5-(hydroxymethyl)furfural (HMF), 2,5-bis(hydroxymethyl)furan (BHMF), and 2,5-furandicarboxylic acid (FDCA) are promising chemical platforms in the biorefinery, which is yet to be explored. The Diels-Alder cycloaddition of BHMF and N-phenylmaleimide derivatives under optimal reaction conditions is investigated in this report. First, HMF is reduced to BHMF in the presence of NaBH4, and then the Diels-Alder reaction of BHMF and N-phenylmaleimide derivatives is investigated to produce Diels-Alder adducts. All novel compounds are synthesized in acceptable yields and effectively characterized by employing important techniques such as one-dimensional (1D) NMR spectroscopy (1H, 13C, DEPT-90, and DEPT- 135), two-dimensional (2D) NMR spectroscopy (1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC), IR spectroscopy, elemental analysis, mass spectrum (QTOF), and single-crystal X-ray diffraction (SC-XRD). Furthermore, this study underlines the necessity of sustainable synthetic methodologies and gives critical insights into the progress of ecologically friendly methodologies, providing a new avenue as a tunable precursor for the challenging functionalized polymer in the future.