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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 11-12
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Original Articles

New Synthesis of Diethyl Auylphosphonates and Diethyl Alkenylphosphonates

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Pages 1891-1898 | Received 30 Aug 1988, Published online: 24 Oct 2006

References

  • Cadogan , J. I. G. 1979 . Organophosphorus Regents in Organic Synthesis , New York : Academic Press .
  • Bhatlacharya , A. K. and Thyagrarajan , G. 1981 . Chem. Ber. , 81 : 415
  • Clark , E. G. R. D. , Kozar , L. B. and Heathcock , C. H. 1975 . Synthesis , : 635
  • Ford-Moore , A. H. and Williams , J. H. 1947 . J. Chem. Soc. , : 1465
  • Koizumi , T. , Tanaka , N. , Iwata , M. and Yoshi , E. 1982 . Synthesis , : 917
  • Hirao , T. , Masunaga , T. , Yamada , Y. , Ohshiro , Y. and Agawa , T. 1982 . Bull. Chem. Soc. Japan , 55 : 909
  • Gupta , A. , Sacks , K. , Khan , S. , Tropp , B. E. and Engel , R. 1980 . Synth. Commun. , 10 : 299
  • Diethyl l-(trimethylsilyl) vinylphosphonate 1 was synthesized by direct coupling of diethyl phosphite and 1-(trimethylsilyl)vinyl bromide in the presence of tetrakis(triphenyl-phosphine) palladium by a modification of the method of Hirao.6 1; Rf(Et20); 0.5, 1H nmr (CDCl3); δ 0.27 (s, 9H), 1.37 (t, J=7Hz 6H), 4.10 (m, 4H). 6.34 (dd, J=58Hz, 3-bHz, 1H), 6.76 (dd, J=34Hz, 3.5Hz, 1H), ir (film); 1250 cm−1, 1030 cm−1, MS (70 eV); 165 (100%), 237 (M+ + 1).
  • Cooke , M. P. Jr. and Widener , R. K. 1987 . J. Am. Chem. Soc. , 109 : 931 and references therein.
  • 1986 . It was reported that α-silyl anions were prone to proton abstraction with enolizable carbonyl compounds. . Ager D. J., l. Chem. Soc., Perkin Trans. , I : 183

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