Reactivity of aldehydes with semi-stabilised arsonium ylide anions: Synthesis of terminal (E)-l,3-dienes

Chemistry - A European Journal

Volumn 13, Issue 19, 2007, Pages 5433-5440

  Habrant, Damien ^a   Stengel, Bruno ^a   Meunier, Stéphane ^a   Mioskowski, Charles ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

1,3 dienes; Alkenes; Arsenic; Olefination; Ylide anions; Ylides

Indexed keywords

ARSENIC; CHEMICAL REACTIVITY; ISOMERS; NEGATIVE IONS; OLEFINS; SYNTHESIS (CHEMICAL);

1,3-DIENES; OLEFINATION; YLIDE ANIONS; YLIDES;

ALDEHYDES;

ALDEHYDE; ALKENE; ANION; ORGANOARSENIC DERIVATIVE;

ARTICLE; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKENES; ANIONS; ARSENICALS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 34547330170     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601549     Document Type: Article

References (35)

1. a) G. Wittig, G. Geissler, Justus Liebigs Ann. Chem. 1953, 550, 44-57
2. b) G. Wittig, U. Schöllkopf, Chem. Ber. 1954, 87,1318-1330.
3. R.W. Hoffmann, Angew. Chem. 2001, 113, 1457-1462;
4. Angew. Chem. Int. Ed. 2001, 40, 1411-1416.
5. B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
6. a) R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728;
7. b) E. Vedejs, H. W. Fang, J. Org. Chem. 1984, 49, 210-212.
8. R. Q. Liu, M. Schlosser, Synlett 1996, 1195-1196.
9. a) R. Q. Liu, M. Schlosser, Synlett 1996, 1197-1198
10. b) Y. Wang, F. G. West, Synthesis 2002, 99-103.
11. Q. Wang, M. El Khoury, M. Schlosser, Chem. Eur. J. 2000, 6, 420-426.
12. H. S. He, C. W. Y. Chung, T. Y. S. But, P. H. Toy, Tetrahedron 2005, 61, 1385-1405.
13. A. W. Johnson, J. O. Martin, Chem. Ind. 1965, 1726-1727.
14. J. D. Hsi, M. Koreeda, J. Org. Chem. 1989, 54, 3229-3231.
15. B. Boubia, C. Mioskowski, Tetrahedron Lett. 1989, 30, 5263-5266.
16. B. Boubia, A. Mann, F. D. Bellamy, C. Mioskowski, Angew. Chem. 1990, 702, 1522-1523;
17. Angew. Chem. Int. Ed. Engl. 1990, 29, 1454-1456.
18. E. G. McKenna, B. J. Walker, Tetrahedron Lett. 1988, 29, 485-488.
19. a) T. Kaufmann, H. Fischer, A. Woltermann, Angew. Chem. 1977, 89, 52-53;
20. Angew. Chem. Int. Ed. Engl. 1977, 16, 53-54;
21. b) T. Kaufmann, H. Fischer, A. Woltermann, Chem. Ber. 1982, 115, 645-653.
22. P.M. Booth, C.M.J. Fox, S.V. Ley, J. Chem. Soc., Perkin Trans. 1 1987, 121-129.
23. H. Daniel, M. Le Corre, Tetrahedron Lett. 1987, 28, 1165-1168.
24. a) M. Schlosser, F. K. Christmann, A. Piskala, D. Coffinet, Synthesis 1971, 29-31
25. b) M. Schlosser, D. Coffinet, Synthesis 1971, 380-381;
26. c) E. J. Corey, H. Yamamoto, J. Am. Chem. Soc. 1970, 92, 226-228.
27. With Ib the reactions were carried out at -78°C.
28. With Id only 2.5 equivalents of base were used.
29. H.-C. Shen, H.-L. Su, Y.-C. Hsueh, R.-S. Liu, Organometallics 2004, 23, 4332-4334.
30. N. Chinkov, S. Majumpar, I. Marek, Synthesis 2004, 14, 2411-2417.
31. K. L. McCaleb, R. L. Halcomb, Org. Lett. 2000, 2, 2631-2634.
32. J. Uenishi, R. Kawahama, O. Yonemitsu, J. Tsuji, J. Org. Chem. 1996, 61, 5716.
33. Y. Ikeda, H. Yamamoto, Bull. Chem. Sot. Jpn. 1986, 59, 657-658.
34. A. Orita, A. Watanabe, H. Tsuchiya, J. Otera, Tetrahedron 1999, 55, 2889-2898.
35. P. L. Wylie, K. S. Prowse, M. A. Belill, J. Org. Chem. 1983, 48, 4022-4025.