1,3‐Dipolar cycloadditions of cyclopentadienones with nitrile TV‐oxides
- 1 June 1979
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 16 (4) , 731-735
- https://doi.org/10.1002/jhet.5570160424
Abstract
The cycloaddition reactions of nitrile oxides with several substituted cyclopentadienones leads to the formation of condensed mono‐isoxazolines (3α,5‐bis‐substituted‐6,6α‐diphenyl‐3αH,4H,6αH‐cyclopenta[2,3‐d]isoxazol‐4‐ones) and in some cases to bis‐isoxazoline derivatives as minor products. The cycloaddition to mono‐adducts is regioselective and only one regioisomer is formed, which can be predicted after consideration of the frontier molecular orbitals of the reacting species. The spectral data of the isoxazolines 3–7 are examined, whereas their structure was fully characterized by X‐ray analysis.Keywords
This publication has 11 references indexed in Scilit:
- The crystal structure of 3-(p-chlorophenyl)-4-oxo-3a,5,6,6a-tetraphenyl-3a,4-dihydrocyclopenta[2,3-d]isoxazolineActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1978
- 1,3-Cycloadditions of 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide to furan, benzofuran, thiophen, and benzothiophenJournal of the Chemical Society, Perkin Transactions 2, 1977
- Selectivity in cycloadditions. 5. Cycloadditions of nitrile oxides to furan. Competing mechanisms and regiochemistryThe Journal of Organic Chemistry, 1976
- 1,3-dipolar cycloadditions of mesitonitrile oxide with substituted cyclobutenedionesTetrahedron Letters, 1976
- Umsetzungen von Cyclopentadienonen mit Diazoalkanen, 8. Versuche mit 2,5‐Diphenyl‐3,4‐di(3‐pyridyl)‐2,4‐cyclo‐pentadien‐1‐onEuropean Journal of Inorganic Chemistry, 1975
- 2-isoxazoline derivatives—VIIITetrahedron, 1974
- Frontier molecular orbitals of 1,3 dipoles and dipolarophilesJournal of the American Chemical Society, 1973
- The Nitrile OxidesPublished by Springer Nature ,1971
- Chemistry of CyclopentadienonesChemical Reviews, 1965
- Dimerization of CyclopentadienonesJournal of the American Chemical Society, 1950