Transformation of alkynyl sulfones into alkynylphosphonates with trialkyl phosphites

Tetrahedron Letters

Volumn 49, Issue 14, 2008, Pages 2265-2267

  Yatsumonji, Yasutaka ^a   Ogata, Akitoshi ^a   Tsubouchi, Akira ^a   Takeda, Takeshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Alkynyl sulfones; Alkynylphosphonates; Arbuzov collapse; Trialkyl phosphites

Indexed keywords

PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 40049104766     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.013     Document Type: Article

References (23)

1. Poss A.J., and Belter R.K. J. Org. Chem. 52 (1987) 4810
2. Corey E.J., and Virgil S.C. J. Am. Chem. Soc. 112 (1990) 6429
3. Guile S.D., Saxton J.E., and Thornton-Pett M. J. Chem. Soc., Perkin Trans. 1 (1992) 1763
4. Cristau H.-J., Mbianda X.Y., Beziat Y., and Gasc M.-B. J. Organomet. Chem. 529 (1997) 301
5. Gil J.M., and Oh D.Y. J. Org. Chem. 64 (1999) 2950
6. Quntar A.A., and Srebnik M. Org. Lett. 3 (2001) 1379
7. Chattha M.S., and Aguiar A.M. J. Org. Chem. 38 (1973) 2908
8. Ruder S.M., and Norwood B.K. Tetrahedron Lett. 35 (1994) 3473
9. Nishida G., Noguchi K., Hirano M., and Tanaka K. Angew. Chem., Int. Ed. 46 (2007) 3951
10. Knierzinger A., Grier A., and Schönholzer P. Helv. Chim. Acta 74 (1991) 517
11. For a review, see:. Iorga B., Eymery F., Carmichael D., and Savignac P. Eur. J. Org. Chem. (2000) 3103
12. Chattha M.S., and Aguiar A.M. J. Org. Chem. 36 (1971) 2719
13. Gil J.M., Sung J.W., Park C.P., and Oh D.Y. Synth. Commun. 27 (1997) 3171
14. For the pioneering work on the synthesis of 1-alkynylphosphonates by the reaction of haloalkynes with phosphites, see:. Ionin B.I., and Petrov A.A. Zhur. Obshch. Khim. 32 (1962) 2387
15. Hägele G., Goudetsidis S., Wilke E., Seega J., Blum H., and Murray M. Phosphorus Sulfur Silicon Relat. Elem. 48 (1990) 131
16. Lodaya J.S., and Koser G.F. J. Org. Chem. 55 (1990) 1513
17. Ogata A., Nemoto M., Kobayashi K., Tsubouchi A., and Takeda T. Eur. J. Org. Chem. (2006) 878
18. Ogata A., Nemoto M., Kobayashi K., Tsubouchi A., and Takeda T. Chem. Eur. J. 13 (2007) 1320
19. Ogata A., Nemoto M., Kobayashi K., Tsubouchi A., and Takeda T. J. Org. Chem. 72 (2007) 3816
20. Bieber L.W., da Silva M.F., and Menezes P.H. Tetrahedron Lett. 45 (2004) 2735
21. Truce W.E., and Brady D.G. J. Org. Chem. 31 (1966) 3543
22. 3P: C, 60.50; H, 6.35. Found: C, 60.73; H, 6.66.
23. Miller S.I., Ziegler G.R., and Wieleseck R. Org. Synth. Coll. Vol. V (1973) 315