Evidence for the non-concerted addition of difluorovinylidene to acetylenes

Chemistry - A European Journal

Volumn 4, Issue 11, 1998, Pages 2360-2365

  Kötting, Carsten ^a   Sander, Wolfram ^a   Senzlober, Michael ^b  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

Alkynes; Carbenes; Matrix isolation; Vinylidene

Indexed keywords

ACETYLENE; ALKYNE; VINYL DERIVATIVE;

ARTICLE; INFRARED SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 0031773392     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981102)4:11<2360::AID-CHEM2360>3.0.CO;2-Y     Document Type: Article

References (24)

1. P. J. Stang, M. G. Mangum, J. Am Chem. Soc. 1975, 97, 3854-3856.
2. W. Sander, A. Kirschfeld, Matrix-Isolation of Strained Three-Membered Ring Systems, Vol. 4 (Ed.: B. Halton), JAI Press. London, 1995, Ch. 2, pp. 1-80.
3. G. L. Closs, Adv. Alicyclic Chem. 1966, 1, 53-127.
4. D. P. Fox, P. J. Stang, Y. Apeloig, M. Karni, J. Am. Chem. Soc. 1986, 108, 750-756.
5. M. S. Lee, J. E. Jackson, Res. Chem. Intermed. 1994, 20(2), 223-247.
6. D. Griller, L. Hadel, A. S. Nazran, M. S. Platz, P. C. Wong, J. C. Scaiano, J. Am. Chem. Soc. 1984, 106, 2227-2235.
7. P. B. Grasse, B. E. Brauer, J. J. Zupancic, K. J. Kaufmann, G. B. Schuster, J. Am. Chem. Soc. 1983, 105, 6833-6845.
8. M. S. Newman, C. D. Beard, J. Org. Chem. 1970, 35(7), 2412-2413.
9. R. J. Norstrom, H. E. Gunning, O. P. Strausz, J. Am. Chem. Soc. 1976, 98, 1454-1461.
10. R. A. Stachnik, G. C. Pimentel, J. Phys. Chem. 1984, 88. 2205-2210.
11. J. C. Brahms, W. P. Dailey, J. Am. Chem. Soc. 1990, 112, 4046-4047.
12. J. E. Jackson, T. A. J. O'Brien, J. Phys. Chem. 1988, 92, 2686-2696.
13. J. Breidung, H. Bürger, C. Kötting, R. Kopitzky, W. Sander, M. Senzlober, W. Thiel, H. Willner, Angew. Chem. 1997, 109, 2072-2075; Angew. Chem. Int. Ed. Engl. 1997, 36, 1983-1985.
14. J. Breidung, H. Bürger, C. Kötting, R. Kopitzky, W. Sander, M. Senzlober, W. Thiel, H. Willner, Angew. Chem. 1997, 109, 2072-2075; Angew. Chem. Int. Ed. Engl. 1997, 36, 1983-1985.
15. C. Kötting, W. Sander, M. Senzlober, H. Bürger, Chem. Eur. J. 1998, 4, 1611-1615
16. C. Kötting, W. Sander, J. Breidung, W. Thiel, M. Senzlober, H. Bürger, J. Am. Chem. Soc. 1998, 120, 219-220.
17. W. E. Billups, L.-J. Lin, E. W. Casserly, J. Am. Chem. Soc. 1984, 106, 3698-3699.
18. B. A. Hess Jr, D. Michalska, L. J. Schaad, J. Am. Chem. Soc. 1985, 107, 1449-1450.
19. E. J. Petersson, J. C. Fanuele, M. R. Nimlos, D. M. Lemal, G. B. Ellison, J. G. Radziszewski, J. Am. Chem. Soc. 1997, 119, 11122-11123.
20. O. L. Chapman, Pure Appl. Chem. 1974, 40, 511-523.
21. R. Albers, W. Sander, J. Org. Chem. 1997, 62, 761-764.
22. R. Albers, W. Sander, Liebigs Ann./Recl. 1997, 897-900.
23. Gaussian 94 (Revision B.3), M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
24. K. B. Wiberg, M. Marquez, J. Am. Chem. Soc. 1998, 120, 2932-2938.