Cycloaddition reactions of 5-hydroxymethyl-furan-2-nitrileoxide
5-Hydroxymethyl-furan-2-nitrileoxide undergoes [3+2] cycloadditions with alkenes to give 3-(2-furanyl)-4,5-dihydo-isoxazole ring system in 71-84% yield. Cycloaddition with one equivalent of dimethylacetylene dicarboxylate gave a 1:1 adduct with 3-(2-furanyl)-isoxazole ring system and further reaction with a second equivalent in a [4+2] Diels-Alder reaction yielded a 3-(7-oxa-bicyclo[2.2.1]hepta-2,5-dien-1-yl)-isoxazole. Hydrogenolysis of 3-(2-furanyl)-4,5-dihydo-isoxazole adducts with Raney-Ni catalyst resulted the ring opening of the 4,5-dihydro-isoxazole ring. © 2007 Bentham Science Publishers Ltd.
Amarasekara, A., Edigin, O., & Hernandez, W. (2007). Cycloaddition reactions of 5-hydroxymethyl-furan-2-nitrileoxide. Retrieved from https://digitalcommons.pvamu.edu/chemistry-physics-facpubs/103