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Isoxazoles from nitrile oxides and acetylenes. Substituent effect on the PMR spectra of disubstituted isoxazoles

1970; Wiley; Volume: 7; Issue: 3 Linguagem: Inglês

10.1002/jhet.5570070347

1943-5193

Arturo Battaglia, Alessandro Dondoni, Fabio Taddei,

Synthesis and properties of polymers

Journal of Heterocyclic ChemistryVolume 7, Issue 3 p. 721-724 Note Isoxazoles from nitrile oxides and acetylenes. Substituent effect on the PMR spectra of disubstituted isoxazoles A. Battaglia, A. Battaglia Laboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, Modena, Ozeano E.-Bologna, Italy and Modena, ItalySearch for more papers by this authorA. Dondoni, Corresponding Author A. Dondoni Laboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, Modena, Ozeano E.-Bologna, Italy and Modena, ItalyLaboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, ModenaSearch for more papers by this authorF. Taddei, F. Taddei Laboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, Modena, Ozeano E.-Bologna, Italy and Modena, ItalySearch for more papers by this author A. Battaglia, A. Battaglia Laboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, Modena, Ozeano E.-Bologna, Italy and Modena, ItalySearch for more papers by this authorA. Dondoni, Corresponding Author A. Dondoni Laboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, Modena, Ozeano E.-Bologna, Italy and Modena, ItalyLaboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, ModenaSearch for more papers by this authorF. Taddei, F. Taddei Laboratorio del C.N.R. dei Composti del Carbonio Contenenti Eteroatomi e loro Applicazioni, Ozzano E.-Bologne, and Istituto di Chimica Organica dell Università, Modena, Ozeano E.-Bologna, Italy and Modena, ItalySearch for more papers by this author First published: June 1970 https://doi.org/10.1002/jhet.5570070347Citations: 17AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat References 2 A. Quilico, in " The Chemistry of Heterocyclic Compounds," Vol. 17, A. Weissberger, Ed., Interscience Publishers, New York, N. Y., 1962, p. 1. 3 N. K. Kochetkov, and S. D. Sokolov, in " Advances in Heterocyclic Chemistry," Vol. II, A. R. Katritzky, Ed., Academic Press, New York, N. Y., 1963, p. 365. 4 R. Huisgen, Angew. Chem. Intern. Ed. Engl., 2, 565 (1963). Angew. Chem. Intern. Ed. Engl., 2, 633 (1963). 5 Ref. 2, p. 8. 6 A. Dondoni, Tetrahedron Letters, 2397 (1967). A. Battaglia and A. Dondoni, Ric. Sci., 38, 201 (1968). 7 P. Beltrame, C. Veglio and M. Simonetta, J. Chem. Soc. (B), 867 (1967). 8 R. Huisgen and M. Christl, Angew Chem. Intern. Ed. Engl., 6, 456 (1967). 9 A. Dondoni, A. Mangini and S. Ghersetti, Tetrahedron Letters, 4789 (1966). G. Barbaro, A. Battaglia and A. Dondoni, J. Chem. Soc. (B), in press. 10 C. Gründmann, Fortschr. Chem. Forsch., 4, 807 (1965). 11 J. V. R. Kaufman and J. P. Picard, Chem. Rev., 59, 429 (1959). 12 T. L. Jacobs, in " Organic Reactions," Vol. 5, R. Adams, Ed., J. Wiley and Sons, New York, N. Y., 1949, p. 1. 13 R. P. Barnes and A. Brandon, J. Am. Chem. Soc., 65, 1070 (1943). 14 G. Bianchi and P. Grünanger, Tetrahedron, 21, 817 (1965). 15 G. Bianchetti, D. Pocar and P. Dalla Croce, Gazz. Chim. Ital., 93, 1714 (1963). 16 C. Weygand, E. Bauer and W. Heynemann, Ann. Chem., 459, 99 (1927). 17 R. W. Bott, C. Eaborn and D. R. M. Walton, J. Chem. Soc., 384 (1965). 18 G. Lo Vecchio and P. Monforte, Gazz. Chim. Ital., 86, 399 (1956). 19 D. Vorländer, Ber., 58, 118 (1925). 20 The exceptionally low yield of this isoxazole is related to the formation of a stable open chain addition by-product. Spectroscopic evidence supports for this compound the structure of acetyl-enic oxime. Similar products have been recently obtained from the reaction of other nitrile oxides with acetylenes (P. Grünanger, A. Ricca and co-workers, Tetrahedron Letters, 3329 (1969)). More details on this subject will be given in due course. 21 A. Baeyer, Ber., 18, 674 (1885). 22 C. Gründmann and J. M. Dean, J. Org. Chem., 30, 2809 (1965). Citing Literature Volume7, Issue3June 1970Pages 721-724 ReferencesRelatedInformation