Synthesis and reactivity of 3-(dialkylamino)allenyl phosphonium salts. PPh3-mediated synthesis of pyrroles from propyne iminium triflates

Arkivoc

Volumn 2007, Issue 3, 2007, Pages 114-131

  Espenlaub, Sigrid ^a   Gerster, Holger ^a   Maas, Gerhard ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Allenylphosphonium salts; Aminoallenes; Conjugate addition; Iminium salts; Pyrroles; Vinylphosphonium salts

Indexed keywords

EID: 33846335186     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.311     Document Type: Article

References (29)

1. Maas, G.; Würthwein, E.-U.; Singer, B.; Mayer, T.; Krauss, D. Chem. Ber. 1989, 122, 2311.
2. Reisser, M.; Maier, A.; Maas, G. Eur. J. Org. Chem. 2003, 2071.
3. Reisser, M.; Maas, G. J. Org. Chem. 2004, 69, 4913.
4. a) Maas, G.; Singer, B.; Wald, P.; Gimmy, M. Chem. Ber. 1988, 121, 1847.
5. b) Rahm, R.; Maas, G. Synthesis 1994, 295.
6. Schlegel, J.; Maas, G. Synthesis 1999, 100.
7. Gerster, H.; Espenlaub, S.; Maas, G. Synthesis 2006, 2251.
8. Schlegel, J.; Maas, G. J. Prakt. Chem. 2000, 342, 235.
9. Mayer, T.; Maas, G.; Synthesis 1991, 1209.
10. Weiss, R.; Wolf, H.; Schubert, U.; Clark, T. J. Am. Chem. Soc. 1981, 103, 6142.
11. Bestmann, H. J.; Schmid, G.; Oechsner, H.; Ermann, P. Chem. Ber. 1984, 117, 1561.
12. (a) Larpent, C.; Meignan, G.; Patin, H. Tetrahedron 1990, 46, 6381.
13. (b) Larpent, C.; Meignan, G.; Patin, H. Tetrahedron Lett. 1991, 32, 2615.
14. (a) Hoffmann, H.; Diehr, H. J. Chem. Ber. 1965, 98, 363.
15. (b) Schweizer, E. E.; Wehman, A. T. J. Chem. Soc. (C) 1970, 1901.
16. Rahm, R.; Espenlaub, S.; Werz, U. R.; Maas, G. Heteroatom Chem. 2005, 16, 437.
17. 31P-NMR-Spektroskopie, Georg Thieme Verlag: Stuttgart, 1993; p 143.
18. (a) Gupton, J. T.; Krolikowski, D. A.; Yu, R. H.; Riesinger, S. W.; Sikorski, J. A. J. Org. Chem. 1990, 55, 4735.
19. (b) Gupton, J. T.; Krolikowski, D. A.; Yu, R. H.; Vu, P.; Sikorski, J. A.; Dahl, M. L.; Jones, C. R. J. Org. Chem. 1992, 57, 5480.
20. (c) Gupton, J.; Petrich, S.; Smith, L. L.; Bruce, M. A.; Vu, P.; Du, K. X.; Dueno, E. E.; Jones, C. R.; Sikorski, J. A. Tetrahedron 1996, 52, 6879.
21. (d) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Dwornik, K. A.; Petrich, S. A.; Du, K. X.; Bruce, M. A.; Vu, P.; Vargas, M.; Keertikar, K. M.; Hosein, K. N.; Jones, C. R.; Sikorski, J. A. Tetrahedron 1998, 54, 5075.
22. (a) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
23. (b) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2265.
24. Yoshida, H.; Utsumi, F.; Suzuki, H.; Ito, S.; Sakashita, S; Ogata, T.; Matsumoto, K. Bull. Chem. Soc. Jpn. 1992, 65, 698.
25. Aoyama, H; Nishio, T.; Hirabayashi, Y.; Hasegawa, T.; Noda, H.; Sugiyama, N. J. Chem. Soc., Perkin Trans. 1 1975, 298.
26. (a) Zakrzewski, J. J. Organomet. Chem. 1987, 333, 71.
27. (b) Periasamy, M.; Srinivas, G.; Bharathi, P. J. Org. Chem. 1999, 64, 4204.
28. Sheldrick, G. M. SHELX-97, University of Göttingen, Germany (1997).
29. Farrugia, L. J. ORTEP-3 for Windows, University of Glasgow, 1998.