Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

• Published in: MolBank Vol. 2024; no. 3; p. M1852
• Main Authors: Quillian, Brandon, Musso, Kennedy, Vinson, Elizabeth M., Bazemore, Joseph G., Marks, Allison R., Padgett, Clifford W.
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 01-09-2024
• Subjects: 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate; 7-oxanorbornene diesters; Alcohol; Analysis; Carboxylic acids; Catalysis; Chemical synthesis; Cyclic compounds; Dicarboxylic anhydride; Diels–Alder; Fischer Esterification; Gas chromatography; Grubb’s catalysis monomer; Identification and classification; Infrared analysis; isoamyl ester; Mass spectrometry; Melting points; Methods; NMR; Nuclear magnetic resonance; Olefins; Polymerization; Single crystals; Structure; Sulfuric acid; Japan
• ISSN: 1422-8599; 1422-8599
• DOI: 10.3390/M1852

Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.