Synthesis of 3-oxo-3-Phenyl-2,2,5-trimethyl-1,3-oxaphosphorinanes and their tetrafluoroborate salts
DOI:
https://doi.org/10.29105/qh1.2-74Palabras clave:
Synthesis, TETRAFLUOROBORATE SALTSResumen
The synthesis and characterization of cis- and trans- 3-oxo-3-phenyl-2,2,5-trimethyl-1,3-oxaphosphorinanes (7a and 7b) and their corresponding tetrafluoroborate salts (3a and 3b) , heterocyclic organophosphorus compounds not previously reported in the literature, was accomplished. They were fully characterized by 1H, 13C and 31PNMR. It was established the relative configuration of these compounds on the basis of an X-ray diffraction study of oxide 7a.
Descargas
Citas
-[1] K. C. Kumara Swamy, N. Satish Kumar, Acc. Chem. Res. 39 (2006) 324. DOI: https://doi.org/10.1021/ar050188x
-[2] (a)Long-Wu Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 37 (2008) 1140. (b) R. Martin, S.L. Buchwald,Acc. Chem. Res. 41 (2008) 1461. (e) B.M. Trost, M.R. Machacek, A. Aponick, Acc. Chem. Res. 39 (2006) 747. (d) T. Baumgartner, R. Reau, Chem. Rev. 106 (2006) 4681.
-[3] (a)A.K.H. Hirsch, F.R. Fischer, F. Diederich, Angew. Chem. Int. Ed. Engl. 46 (2007) 338. (b) Z.Y. Zhang, Acc. Chem. Res. 36 (2003) 385. (e) Y. Takagi, M. Warashima, W.J. Stec, K. Yoshinari, K. Taira, NucleicAcid Res. 29 (2001) 1815. (d) R.T . Raines, Chem. Rev. 98 ( 1998) 1045. (e) D.M. Perreault, E. V. Anslyn, Angew. Chem. Int. Ed. Engl. 36 (1997) 43 3.
-[4] (a) P.A. Frey, Tetrahedron 38 (1982) 1541. (b) K. Bruzik, M.D. Tsai, J. Am. Chem. Soc. 106 (1984) 747. (e) W.E. McEwen, K.F. Kumli, A. Blade-Font, M. Zanger, C.A. Vander Werf, J. Am. Chem. Soc. 86 (1964) 2378. (d) M. Zanger, C.A. VanderWerf, W.E. McEwen, J. Am. Chem. Soc. 81 (1959) 3806. (e) L. Horner, H. Winkler, A. Rapp, A. Mentrup, H. Hoffmann, P. Beck, Tetrahedron Lett. ( 1961) 161.
-[5] (a) 0.1. Kolodiazhnyi, Tetrahedron:Asymm 9 (1998) 1279. (b) R. Z. Luckenbach, Naturforsch3 lb(1976) 1127. (c)G. Zon, K.E. De Bruin, K. Naumann, K. Mislow, J. Am. Chem. Soc. 91 (1969) 7023. (d) R. Luckenbach, Phosphorus 1 (1972) 223. (e) R. Luckenbach, Phosphorus 1 (1972) 229.
-[6] K.L. Marsi, R.T. Clark, J. Am. Chem. Soc. 92 (1970) 3791. DOI: https://doi.org/10.1021/ja00715a045
-[7] K.L. Marsi, J. Org. Chem. 40 (197 5) 17 79.
-[8] S. López-Cortina, D.I. Basiulis, K.L. Marsi, M.A. Muñoz-Henández, M. Ordoñez, M. Fenández-Zertuche, J. Org. Chem. 70 (2005) 7473. DOI: https://doi.org/10.1021/jo050901w
-[9] K.L. Marsi, M.E. Co-Samo, J. Org. Chem. 42 (1977) 778. DOI: https://doi.org/10.1021/jo00425a002
-[10] K . Issleib, H.R. Roloff, Chem. Ber. 98 (1965) 2091. DOI: https://doi.org/10.1002/cber.19650980707
-[11] Purification of Laboratory Chemicals; Perrin, D.D., Armarego, W.L.F., Pergamon Press, 3rd. ed, Great Britain (1989).
-[12] D.B. Denney, J.W.Jr. Hanifin, Tetrahedron Lett. (1963) 2177. DOI: https://doi.org/10.1016/S0040-4039(01)90991-8
-[13] S.Jr. Searles, K.A. Pollart, F. Block,J.Am. Chem. Soc. 79 (1957) 952. DOI: https://doi.org/10.1021/ja01570a028
-[14] W. Kuchen, H. Buchwald, Chem. Ber. 91 (1958) 2296. DOI: https://doi.org/10.1002/cber.19580911107
-[15] (a) H. Oehme, K. Issleib, E. Leissring, Tetrahedron 28 (1972) 2587. (b) K. Issleib, H. Oehme, M. Scheibe, Syn. Inorg. Metal-Org. Chem. 2 (1972) 223. (e) A. Zschunke, H. Meyer, E. Leissring, H. Oehme, K. Issleib, Phosphorus and Sulfur 5 (1978) 81. DOI: https://doi.org/10.1016/0040-4020(72)80093-0
-[16] (a) D.J. Hodgson, U. Rychlewska, E.L. Eliel, M. Manoharan, D.E. Knox, E.M. Olefirowicz, J. Org.Chem. 50 (1985) 4838. (b) K.B. Wiberg, H. Castejon, W.F. Bailey, J. Ochterski, J.Org.Chem. 65 (2000) 1181. (e) Stereochemistry of Organic Compounds; Eliel, E.L., Wilen, S.H., John Wiley and Sons, Inc., New York, (1994).
-[17] (a) N.L. Allinger, H. von Voithenberg, Tetrahedron 34 (1978) 627. (b) A.T. McPhail, J. J. Breen, L.D. Quin, J.Am.Chem.Soc. 93 (1971) 2574. (e) J.B. Rampal, J.B.; K.D. Berlin, J.P. Edasery, H. Satyamurthy, J.Org.Chem. 46 (1981) 1166.
-[18] (a) A. Rudi, Y. Kashman, Tetrahedron Lett. ( 1978) 2209. (b) R. Bodalski, K.M. Pietrusiewicz, J. Koszuk, Tetrahedron 31 (1975) 1907. (e) G.A. Gray, S.E. Cremer, K.L. Marsi, J.Am.Chem.Soc. 98 (1976)2109.
-[19] (a) H. Meerwein, Org. Syn. 6 (1966) 120. (b) H.W. Heine, T.A. Newton, G.J. Blosick, K.C. Irving, C. Meyer, G.B. Corcoran III, J. Org. Chem. 3 8 (1973) 651. (e) von H. Hellman, J. Bader, H. Birkner, und O. Schumacher, Liebigs Ann. Chem. 48 (1962) 659. (d) H.O. House, F.A.jr. Richey, J. Org. Chem. 34 (1969) 1430. (e) K.L. Marsi, J.L. Jasperse, J.Org.Chem. 43 ( 1978) 7 60. (f ) G. Zon, K.E. DeBruin, K. Naumann, K. Mislow, J .Am. Chem. Soc. 91 ( 1969) 7023.
Descargas
Publicado
Cómo citar
Número
Sección
Licencia
Derechos de autor 2011 Susana López Cortina , Perla Elizondo Martínez , Nancy Pérez Rodríguez , Eugenio Hernández Fernández , Mario Fernández Zertuche
Esta obra está bajo una licencia internacional Creative Commons Atribución 4.0.
