1,2-Addition Reaction of a Protic Phosphonium Cation with a Phosphaalkyne

Inorganic Chemistry

Volumn 35, Issue 10, 1996, Pages 3062-3063

  Clyburne, Jason A C ^a   Schriver, Melbourne J ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0043116592     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic951132+     Document Type: Article

References (32)

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5. For reviews, see: (a) Regitz, M.; Binger, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1484-1508. (b) Regitz, M. Chem. Rev. 1990, 90, 191-213. (c) Regitz, M. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: New York, 1990; pp 58-89. (d) Regitz, M. Bull. Soc. Chim. Belg. 1992, 101, 359-379.
6. For reviews, see: (a) Regitz, M.; Binger, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1484-1508. (b) Regitz, M. Chem. Rev. 1990, 90, 191-213. (c) Regitz, M. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: New York, 1990; pp 58-89. (d) Regitz, M. Bull. Soc. Chim. Belg. 1992, 101, 359-379.
7. For reviews, see: (a) Regitz, M.; Binger, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1484-1508. (b) Regitz, M. Chem. Rev. 1990, 90, 191-213. (c) Regitz, M. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: New York, 1990; pp 58-89. (d) Regitz, M. Bull. Soc. Chim. Belg. 1992, 101, 359-379.
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10. +. See Parsons, S.; Passmore, J.; Sun, X. Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 93-94, 435-436.
11. A methylene phosphonium cation has been reported. See, for example: Igau, A.; Bacereido, H.; Grutzmacher, H.; Pritzkow, H.; Bertrand, G. J. Am. Chem. Soc. 1989, 111, 6853-6854.
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14. See, for example: (a) Reed, R.; Reau, R.; Dahan, F.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 399-401. (b) Burford, N.; Losier, P.; Sereda, S. V.; Cameron, T. S.; Wu, G. J. Am. Chem. Soc. 1994, 116, 6474-6475.
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19. 13C NMR spectra were calibrated to the internal solvent signal.
20. 13C NMR spectra were calibrated to the internal solvent signal.
21. 13C NMR spectra were calibrated to the internal solvent signal.
22. 13C NMR spectra were calibrated to the internal solvent signal.
23. 13C NMR spectra were calibrated to the internal solvent signal.
24. 2 solution.
25. Kalinowski, H. O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: New York, 1981.
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27. Lambert, J. B.; Schurvell, H. F.; Lightner, D.; Cooks, R. G. In Introduction to Organic Spectroscopy; Macmillan Publishing Company: New York, 1987; Chapter 5.
28. 31P 22 ppm).
29. Newcome, G. R.; Roper, J. M. J. Org. Chem. 1979, 44, 502-505.
30. See, for example, (a) Shirafuji, T.; Yamamoto, Y.; Nozaki, H. Tetrahedron 1971, 27, 53353-5358; (b) Shirafuji, T.; Kitatini, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1973, 46, 2249-2251.
31. See, for example, (a) Shirafuji, T.; Yamamoto, Y.; Nozaki, H. Tetrahedron 1971, 27, 53353-5358; (b) Shirafuji, T.; Kitatini, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1973, 46, 2249-2251.
32. 15C≡P). A small signal (< 10%) was observed at 412 ppm (unknown).