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The Mechanism of the Bischler‐Napieralski Reaction

1972; Wiley; Volume: 11; Issue: 10 Linguagem: Inglês

10.1002/anie.197209191

1521-3773

Gábor Fodor, J. Gál, Barry A. Phillips,

Oxidative Organic Chemistry Reactions

Angewandte Chemie International Edition in EnglishVolume 11, Issue 10 p. 919-920 Communication The Mechanism of the Bischler-Napieralski Reaction† Prof. Dr. Gábor Fodor, Prof. Dr. Gábor Fodor Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Search for more papers by this authorDr. J. Gal, Dr. J. Gal Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Search for more papers by this authorB. A. Phillips, Corresponding Author B. A. Phillips Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Search for more papers by this author Prof. Dr. Gábor Fodor, Prof. Dr. Gábor Fodor Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Search for more papers by this authorDr. J. Gal, Dr. J. Gal Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Search for more papers by this authorB. A. Phillips, Corresponding Author B. A. Phillips Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506 (USA)Search for more papers by this author First published: October 1972 https://doi.org/10.1002/anie.197209191Citations: 53 † Acknowledgment is made to the donors of the Petroleum Research Fund administered by the American Chemical Society for support of this work and also to the Research Corporation. AboutPDF 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 No abstract is available for this article. References 1 Acknowledgment is made to the donors of the Petroleum Research Fund administered by the American Chemical Society for support of this work and also to the Research Corporation. 2 J. v. Braun, Ber. Dtsch. Chem. Ges. 37, 2915 (1904); H. v. Pechmann, Ber. Dtsch. Chem. Ges. 33, 611 (1900). 3 B. A. Phillips and G. Fodor, 162nd ACS National Meeting, Washington 1971, Paper ORGN 019. 4 B. A. Phillips, Dissertation, West Virginia University 1972. 5 H. Ulrich: The Chemistry of Imidoyl Halides. Plenum Press, New York 1968. 6 J. Gal, B. A. Phillips, and R. Smith, Can. J. Chem., in press. 7 I. Ugi, F. Beck, and V. Fetzer, Chem. Ber. 95, 125 (1962) found an initial first-order kinetics in the hydrolysis of imidoyl chlorides which they ascribed to the formation of a nitrilium ion in the rate-determining step. 8 According to H. Decker and W. Kropp, Ber. Dtsch. Chem. Ges. 42, 2075 (1909), so-called unactivated phenylethylamides cyclize under the action of phosphorus pentachloride and (subsequently) of aluminum chloride. Furthermore, H. J. Barber et al., J. Soc. Chem. Ind. 69, 82 (1950) isolated an imidoyl chloride during the synthesis of phenylanthridines. 9 M. Lora-Tamayo and R. Madronero et al., Chem. Ber. 94, 199 (1961). 10 J. J. Ritter and P. P. Minieri, J. Amer. Chem. Soc. 70, 4045, 4048 (1948). 11 A. McCoubrey and D. W. Mathieson, J. Chem. Soc. 1949, 696: A. J. Hill and W. M. Halliday, ACS National Meeting, Chicago 1950, Paper 58N. 12 W. M. Whaley and T. R. Govindachari, Org. Reactions 6, 74 (1951). Citing Literature Volume11, Issue10October 1972Pages 919-920 ReferencesRelatedInformation