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The site of protonation in phosphole derivatives. 1 H ‐Phospholium salts stabilized by complex transition metal ions

1971; Wiley; Volume: 8; Issue: 5 Linguagem: Inglês

10.1002/jhet.5570080542

1943-5193

R. Chuchman, David G. Holah, A. N. HUGHES, B. C. HUI,

Organophosphorus compounds synthesis

Journal of Heterocyclic ChemistryVolume 8, Issue 5 p. 877-879 Communication to the Editor The site of protonation in phosphole derivatives. 1H-Phospholium salts stabilized by complex transition metal ions R. Chuchman, R. Chuchman Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this authorD. G. Holah, D. G. Holah Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this authorA. N. Hughes, A. N. Hughes Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this authorB. C. Hui, B. C. Hui Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this author R. Chuchman, R. Chuchman Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this authorD. G. Holah, D. G. Holah Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this authorA. N. Hughes, A. N. Hughes Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this authorB. C. Hui, B. C. Hui Department of Chemistry, Lakehead University, Thunder Bay, Ontario, CanadaSearch for more papers by this author First published: October 1971 https://doi.org/10.1002/jhet.5570080542Citations: 12AboutPDF 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 1 D. A. Brown, J. Chem. Soc., 929 (1962). 2 G. Märkl and R. Potthast, Tetrahedron Letters, 1755 (1968). 3 L. D. Quin and J. G. Bryson, J. Am. Chem. Soc., 89, 5984 (1967). 4 L. D. Quin, J. G. Bryson and C. G. Moreland, J. Am. Chem. Soc., 91, 3308 (1969). 5 W. Egan, R. Tang, G. Zon and K. Mislow, J. Am. Chem. Soc., 92, 1442 (1970). 6 For a brief discussion of the aromatic character of phosphole derivatives see the review by A. N. Hughes and C. Srivanavit, J. Heterocyclic Chem., 7, 1 (1970). 7 Y. Chiang and E. B. Whipple, J. Am. Chem. Soc., 85, 2763 (1963). 8 D. E. C. Corbridge, Topics in Phosphorus Chemistry, 6, 235, (1969). 9 K. W. Bagnall and D. Brown, J. Chem. Soc., 3021 (1964). 10 A. F. Bedford, D. M. Heinekey, I. T. Millar and C. T. Mortimer, J. Chem. Soc., 2932 (1962). 11 We are indebted to a referee for pointing out that what is actually being protonated (for niobium and tantalum) is a phosphole complex of the metal halide. However, in the case of iron (III), where protonation clearly occurs (although no pure complex was isolated), there is no coordination between iron (III) chloride and the phosphole (12). We therefore feel that the metal plays no part in the protonation process except in so far as the anion appears to stabilize the protonated phosphole once the latter has formed. 12 D. Budd, R. Chuchman, D. G. Holah, A. N. Hughes and B. C. Hui, to be published. Citing Literature Volume8, Issue5October 1971Pages 877-879 ReferencesRelatedInformation