Formation of O-allyl oximes by reaction of allylzinc reagents with α-chloronitroso compounds

Synthesis

Volumn , Issue 20, 2005, Pages 3565-3570

  Filip, Sorin V ^a,b   Sewald, Norbert ^a  

^a BIELEFELD UNIVERSITY   (Germany)

^b Highfield Road Industrial Estate   (United Kingdom)

Author keywords

Allylations; Ene reactions; Organometallic reagents; Regioselectivity; Zinc

Indexed keywords

ALKYLATION; AROMATIC COMPOUNDS; NITROGEN COMPOUNDS; TOLUENE; ZINC;

ALLYLATIONS; ENE REACTIONS; ORGANOMETALLIC REAGENTS; REGIOSELECTIVITY;

REACTION KINETICS;

ALLYL COMPOUND; CHLORINE DERIVATIVE; CYCLOHEXANE DERIVATIVE; HALIDE; HYDROGEN; HYDROXYLAMINE; NITRONE DERIVATIVE; NITROSO DERIVATIVE; OXIME; REAGENT; TETRAHYDROFURAN; TOLUENE; ZINC DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; ELIMINATION REACTION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 29744454127     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918429     Document Type: Article

References (28)

1. Adam, W.; Krebs, O. Chem. Rev. 2003, 103, 4131.
2. (a) Leach, A. G.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 14820.
3. (b) Leach, A. G.; Houk, K. N. Chem. Commun. 2002, 1243.
4. (c) Leach, A. G.; Houk, K. N. Org. Biomol. Chem. 2003, 1, 1389.
5. Lu, X. Org. Lett. 2004, 6, 2813.
6. Banks, R. E.; Barlow, M. G.; Haszeldine, R. N. J. Chem. Soc. 1965, 4714.
7. (a) Schenk, C.; de Boer, T. J. Tetrahedron 1979, 35, 147.
8. (b) Schenk, C.; de Boer, T. J. Recl. Trav. Chim. Pays-Bas 1979, 98, 18.
9. Kresze, G.; Vasella, A.; Felber, H.; Ritter, A.; Ascherl, B. Recl. Trav. Chim. Pays-Bas 1986, 105, 295.
10. (a) Oppolzer, W.; Tamura, O.; Sundarababu, G.; Signer, M. J. Am. Chem. Soc. 1992, 114, 5900.
11. (b) Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta 1992, 75, 1965.
12. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38;
13. Angew. Chem. 1989, 101, 39.
14. (a) Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743.
15. (b) Dang, H.-S.; Davies, A. G. J. Organomet. Chem. 1992, 430, 287.
16. (c) Davies, A. G. J. Chem. Soc., Perkin Trans. 1 2000, 1997.
17. (d) Dang, H.-S.; Davies, A. G. J. Organomet. Chem. 1998, 553, 67.
18. Aston, J. G.; Menard, D. F. J. Am. Chem. Soc. 1935, 57, 1920.
19. Miyabe, H.; Matsumura, A.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. Synlett 2004, 2123.
20. (a) Schenk, C.; Beekes, M. L.; de Boer, T. J. Recl. Trav. Chim. Pays-Bas 1980, 99, 246.
21. (b) Schenk, C.; Beekes, M. L.; van der Drift, J. A. M.; de Boer, T. J. Recl. Trav. Chim. Pays-Bas 1980, 99, 278.
22. (c) Schenk, C.; de Boer, T. J. Tetrahedron 1980, 36, 1843.
23. Barbot, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1977, 1-2, 113.
24. Erdik, E. Organozinc Reagents in Organic Synthesis; CRC Press: Boca Raton, FL, 1996, 147.
25. Rieke, R. D. Aldrichimica Acta 2000, 33, 52.
26. Diekmann, H.; Luettke, W. Angew. Chem. 1968, 80, 395.
27. 2, 0 °C, 1.5 h. Diagram presented.
28. Müller, E.; Metzger, H.; Fries, D. Chem. Ber. 1954, 87, 1449.