A convenient approach to λ5-phosphinines via interaction of phosphorylated 3-pyrrolidinocrotonitrile with 2-bromoacetophenones

Tetrahedron

Volumn 63, Issue 25, 2007, Pages 5656-5664

  Svyaschenko, Yurii V ^a   Kostyuk, Alexandr N ^a   Barnych, Bogdan B ^a   Volochnyuk, Dmitriy M ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

5 Phosphinines; 2 Bromoacetophenones; Phosphonium salts; Phosphorylated enamines

Indexed keywords

ACETOPHENONE DERIVATIVE; BROMINE DERIVATIVE; NITRILE; PHOSPHONIUM DERIVATIVE; SODIUM CHLORIDE;

ALKYLATION; ARTICLE; CATALYSIS; CYCLIZATION; HEATING; PHOSPHORYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 34248596550     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.172     Document Type: Article

References (46)

1. Quin L.D. The Heterocyclic Chemistry of Phosphorus Systems Based on the Phosphorus-Carbon Bond (1981), Wiley, New York, NY
2. Mathey F.J. In: Grayson M., and Griffith E.J. (Eds). Topics in Phosphorus Chemistry Vol. 10 (1980), Wiley, New York, NY 1-128
3. Mader M.M., and Bartlett P.A. Chem. Rev. 97 (1997) 1281-1301
4. Dillon K.B., Mathey F., and Nixon J.F. Phosphorus: The Carbon Copy (1998), Wiley, Chichester, UK Chapters 8 and 9
5. Madsen G.K.H., Krebs F.C., Lebech B., and Larsen F.K. Chem.-Eur. J. 6 (2000) 1797-1804
6. Toshimitsu A., Saeki T., and Tamao K. J. Am. Chem. Soc. 123 (2001) 9210-9211
7. Edwards P.G., Paisey S.J., and Tooze R.P. J. Chem. Soc., Perkin Trans. 1 (2000) 3122-3128
8. Heinike J., Gupta N., Surana A., Peulecke N., Witt B., Steinhauser K., Bansal R.K., and Jones P.G. Tetrahedron 57 (2001) 9963-9972
9. In: Mathey F. (Ed). Applications of Phosphorus Heterocycles in Homogeneous Catalysis. Phosphorus-Carbon Heterocyclic Chemistry (2001), Pergamon, Oxford 753-772
10. Herwig, J.; Bohnen, H.; Skutta, P.; Sturm, S.; Van Leeuwen, P. W. N. M.; Bronger, R. WO 0268434, 2002;
11. Chem. Abstr. 137 (2002) 201440
12. Karacar A., Freytag M., Jones P.G., Bartsch R., and Schmutzler R. Z. Anorg. Allg. Chem. 627 (2001) 1571-1581
13. Kenten, J. H.; Von Borstel, R.; Casadei, J. M.; Kamireddy, B.; Martin, M. T.; Massey, R. J.; Napper, A. D.; Simpson, D. M.; Smith, R. G.; Titmas, R. C.; Williams, R. O. U.S. Patent 740501, 1993;
14. Chem. Abstr. 119 (1993) 210716
15. Hirai, Y.; Suzuki, H.; Takeda, Y. JP 2003049051, 2003;
16. Chem. Abstr. 138 (2003) 154807
17. Chikamasa, N. JP 2003041473, 2003;
18. Chem. Abstr. 138 (2003) 138749
19. Krebs F.C., Larsen P.S., Larsen J., Jacobsen C.S., Boutton C., and Thorup N. J. Am. Chem. Soc. 119 (1997) 1208-1216
20. Mizukura, N.; Kita, H. JP 04029237, 1992;
21. Chem. Abstr. 117 (1992) 17188
22. Martinek T., Forro E., Günther G., Sillanpää R., and Fülöp F. J. Org. Chem. 65 (2000) 316-321
23. Bujard M., Gouverneur V., and Mioskowski C. J. Org. Chem. 64 (1999) 2119-2123
24. Hoffmann, M. G.; Bauer, K.; Bieringer, H.; Rosinger, C.; Lindell, S. D. DE 19542305, 1997;
25. Chem. Abstr. 127 (1997) 5196
26. Dimroth K. Fortschr. Chem. Forsch. 38 (1973) 1-147
27. Markl G. Angew. Chem. 75 (1963) 669
28. Angew. Chem., Int. Ed. Engl. 2 (1963) 479
29. Markl G., Baier H., and Liebl R. Synthesis (1977) 842-845
30. Markl G., Liebl R., and Huttner A. Angew. Chem. 90 (1978) 566-567
31. Angew. Chem., Int. Ed. Engl. 17 (1978) 528-530
32. Markl G., Baier H., Liebl R., and Stephenson D.S. Liebigs Ann. Chem. (1981) 870-918
33. Markl G., Hock K., and Matthes D. Chem. Ber. 116 (1983) 445-472
34. Kostyuk A.N., Svyaschenko Y.V., and Volochnyuk D.M. Tetrahedron 61 (2005) 9263-9272
35. Kostyuk A.N., Svyaschenko Y.V., Volochnyuk D.M., Lysenko N.V., Tolmachev A.A., and Pinchuk A.M. Tetrahedron Lett. 44 (2003) 6487-6491
36. Hoffmann H., and Diehr H.J. Angew. Chem., Int. Ed. Engl. (1964) 737
37. Kolodiazhnyi O.I. Phosphorus Ylides: Chemistry and Application in Organic Synthesis (1999), Wiley-VCH, Weinheim, New York, Chichester, UK
38. Volochnyuk D.M., Kostyuk A.N., Sibgatulin D.A., Chernega A.N., Pinchuk A.M., and Tolmachev A.A. Tetrahedron 60 (2004) 2361-2371
39. Mukhanova T.I., Alekseeva L.M., and Granik V.G. Chem. Heterocycl. Compd. (Engl. Transl.) 39 (2003) 156-160
40. 3SiCl as a water scavenger, see:
41. Ryabukhin S.V., Plaskon A.S., Volochnyuk D.M., and Tolmachev A.A. Synlett (2004) 2287-2290
42. Ryabukhin S.V., Plaskon A.S., Volochnyuk D.M., and Tolmachev A.A. Synthesis (2006) 3715-3726
43. Petnehazy I., Szakal G., Toke L., Hudson H.R., Powroznyk L., and Cooksey C.J. Tetrahedron 39 (1983) 4229-4235
44. Yamamoto I., Tashiro K., Uchiyama T., and Fujimoto T. Phosphorus, Sulfur Silicon Relat. Elem. 148 (1999) 11-20
45. Appel R., and Waid K. Z. Naturforsch., B: Anorg. Chem. Org. Chem. 36 (1981) 131-134
46. Ivanov B.E., Krokhina S.S., Chichkanova T.V., and Kosacheva E.M. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 34 (1985) 162-167