Organophosphorus Compounds; 106. 1 Tandem Ene Reactions of Phosphaalkynes with Terminal Alkenes as All-Carbon Enes

Synthesis

Volumn , Issue 1, 1996, Pages 100-104

  Mackewitz, Thomas W ^a   Regitz, Manfred ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030058774     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4165     Document Type: Article

References (22)

1. Part 105, see: Laali, K. K.; Geißler, B.; Regitz, M.; Hauser, J. J. J. Org. Chem. 1995, 60, in press.
2. For general reviews of ene reactions in carbon chemistry see: Hoffmann, H. M. R. Angew. Chem. 1969, 81, 597; Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Boyd, G. V. In The Chemistry of Double-Bonded Functional Groups, Vol. 2, Part 1; Patai, S., Ed.; J. Wiley: New York, 1989; p477. Snider, B. B. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 1.
3. For general reviews of ene reactions in carbon chemistry see: Hoffmann, H. M. R. Angew. Chem. 1969, 81, 597; Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Boyd, G. V. In The Chemistry of Double-Bonded Functional Groups, Vol. 2, Part 1; Patai, S., Ed.; J. Wiley: New York, 1989; p477. Snider, B. B. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 1.
4. For general reviews of ene reactions in carbon chemistry see: Hoffmann, H. M. R. Angew. Chem. 1969, 81, 597; Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Boyd, G. V. In The Chemistry of Double-Bonded Functional Groups, Vol. 2, Part 1; Patai, S., Ed.; J. Wiley: New York, 1989; p477. Snider, B. B. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 1.
5. For general reviews of ene reactions in carbon chemistry see: Hoffmann, H. M. R. Angew. Chem. 1969, 81, 597; Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Boyd, G. V. In The Chemistry of Double-Bonded Functional Groups, Vol. 2, Part 1; Patai, S., Ed.; J. Wiley: New York, 1989; p477. Snider, B. B. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 1.
6. Reviews: Regitz, M. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M.; Scherer, O. J., Eds.; Thieme: Stuttgart, 1990; p 58. Regitz, M. Chem. Rev. 1990, 90, 191.
7. Reviews: Regitz, M. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M.; Scherer, O. J., Eds.; Thieme: Stuttgart, 1990; p 58. Regitz, M. Chem. Rev. 1990, 90, 191.
8. Fuchs, E. P. O.; Rösch, W.; Regitz, M. Angew. Chem. 1987, 99, 1058; Angew. Chem., Int. Ed. Engl. 1987, 26, 1011.
9. Fuchs, E. P. O.; Rösch, W.; Regitz, M. Angew. Chem. 1987, 99, 1058; Angew. Chem., Int. Ed. Engl. 1987, 26, 1011.
10. Heydt, H.; Bergsträßer, U.; Fäßler, R.; Fuchs, E.; Kamel, N.; Mackewitz, T.; Michels, G.; Rösch, W.; Regiz, M.; Mazerolles, P.; Laurent, C.; Faucher, A. Bull. Soc. Chim. Fr. 1995, 132, 652.
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12. Breit, B. ; Boese, R.; Regitz, M. J. Organomet. Chem. 1994, 464, 41.
13. Ene reactions of this type could also be directly realized by using pentacarbonyltungsten complexes of phosphaalkenes: Marinetti, A.; Ricard, L.; Mathey, F.; Slany, M.; Regitz, M. Tetrahedron 1993, 49, 10279.
14. Annen, U.; Regitz, M. Tetrahedron Lett. 1988, 29, 1681.
15. Alder, K.; Pascher, F.; Schmitz, A. Ber. Dtsch. Chem. Ges. 1943, 76, 27.
16. Maier, L.; Diehl, P. J.; Tebby, J. C. In CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data; Tebby, J. C., Ed.; CRC: Florida, 1991; p 134.
17. N. M. R. Standard Spectra, Vol. 23; Sadtler Research Laboratories Inc.: Philadelphia, 1973; 14676M
18. Hall, M. C.; Kinns, M.; Wells, E. J. Org. Magn. Reson. 1983, 21, 108.
19. 31P NMR spectra of the reaction mixtures the specific formation of only one product and no byproducts was observed.
20. Rösch, W.; Hees, U.; Regitz, M. Chem. Ber. 1987, 120, 1645.
21. Regitz, M.; Rösch, W.; Allspach, T.; Annen, U.; Blatter, K.; Fink, J.; Hermesdorf, M.; Heydt, H.; Vogelbacher, U.; Wagner, O. Phosphorus Sulfur 1987, 30, 479.
22. Allspach, T.; Regitz, M.; Becker, G.; Becker, W. Synthesis 1986, 31.