Synthesis of 3-oxo-3-Phenyl-2,2,5-trimethyl-1,3-oxaphosphorinanes and their tetrafluoroborate salts
DOI:
https://doi.org/10.29105/qh1.2-74Keywords:
Synthesis, TETRAFLUOROBORATE SALTSAbstract
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.
Downloads
References
-[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.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2011 Susana López Cortina , Perla Elizondo Martínez , Nancy Pérez Rodríguez , Eugenio Hernández Fernández , Mario Fernández Zertuche
This work is licensed under a Creative Commons Attribution 4.0 International License.
