Evidence for a continuous transition between thiaphosphetane and betaine-type structures in the thio-wittig reaction

Journal of the American Chemical Society

Volumn 120, Issue 19, 1998, Pages 4863-4864

  Puke, Carsten ^a   Erker, Gerhard ^a   Aust, Nicola C ^a   Würthwein, Ernst Ulrich ^a   Fröhlich, Roland ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000775741     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9720669     Document Type: Article

References (25)

1. For reviews, see: Schlosser, M. Top. Stereochem. 1970, 5, 1.
2. Maryanoff, B. E.; Reitz, A. E. Chem. ReV. 1989, 89, 863.
3. Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1.
4. Vedejs, E.; Marth, C. F. In Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis; Quin, L. D., Verkade, J. E., Eds.; VCH: New York, 1994; pp 297-313.
5. (a) For NMR studies, see: Vedejs, E.; Snoble, K. A. J. J. Am. Chem. Soc. 1973, 95, 5778
6. Vedejs, E.; Meier, G. P.; Snoble, K. A. J. J. Am. Chem. Soc. 1981, 103, 2823.
7. Maryanoff, B. E.; Reitz, A. B.; Mutter, M. S.; Inners, R. R.; Almond, H. R., Jr.; Whittle, R. R.; Olofson, R. A. J. Am. Chem. Soc. 1986, 108, 7664
8. Maryanoff, B. E.; Reitz, A. B. Phosphorus Sulfur 1986, 27, 167
9. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3940.
10. Geletneky, C.; Försterlin, F.-H.; Bock, W.; Berger, S. Chem. Ber. 1993, 126, 2397
11. (b) For X-ray crystal structure analyses, see: Kawashima, T.; Kato, K.; Okazaki R. J. Am. Chem. Soc. 1992, 114, 4008;
12. Angew. Chem. 1993, 105, 941;
13. Angew. Chem., Int. Ed. Engl. 1993, 32, 869 and references therein.
14. For a Review, see: Kawashima, T.; Okazaki, R. Synlett 1996, 600.
15. For a comprehensive review of this development, see: Vedejs, E.; Peterson, M. J. In AdVances in Carbanion Chemistry: Snieckus, V., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 1-85, and references therein.
16. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1990, 112, 3905.
17. Wilker, S.; Laurent, C.; Sarter, C.; Puke, C.; Erker, G. J. Am. Chem. Soc. 1995, 117, 7293
18. Okuma, K.; Ishida, T.; Morita, S.; Ohta, H.; Inoue, T. Heteroat. Chem. 1995, 6, 265.
19. For other recent calculations on the Wittig reaction, see, e.g.: Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1.
20. Mari, F.; Lahti, P. M.; McEwen, W. E. J. Am. Chem. Soc. 1992, 114, 813 and references therein.
21. Borisova, I. V. Zemlyanskii, N. N.; Shestakova, A. K.; Ustynyuk, Y. A. MendeleeV Commun. 1996, 90. A structurally related stabilized betaine, obtained by addition of Ph3PdC(CH3)2 to carbon disulfide, was characterized by X-ray diffraction
22. Kunze, U.; Merkel, R.; Winter, W. Chem. Ber. 1982, 115, 3653
23. Schaumann, E.; Grabley, F.-F. Liebigs Ann. Chem. 1979, 1702
24. Bestmann, H. J.; Engler, R.; Hartung, H.; Roth, K. Chem. Ber. 1979, 112, 28.
25. Bondi, A. J. Phys. Chem. 1964, 68, 441.