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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 16
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Original Articles

Reaction of Pummerer Rearrangement Intermediate with Thiols: New Synthetic Method of S,S-Thioacetals of Formylphosphonate

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Pages 2313-2318 | Received 07 Dec 1993, Published online: 23 Sep 2006

References

  • Walker , B. J. 1979 . Organophosphorus Reagents in Organic Synthesis , Edited by: Cadogan , J. I. G. New York : Academic Press . Chater 3.
  • Wadsworth , W. S. Jr. 1977 . Org. React. , 25 : 73
  • Maryanoff , B. E. and Reitz , A. B. 1989 . Chem. Rev. , 89 : 863
  • Kelly , S. E. 1991 . Comprehensive Organic Synthesis, Addition to C-X π Bonds, Part 1 , Edited by: Schreiber , S. L. Vol. 1 , Oxford : Pergamon Press . Chapter 3.1.
  • Mikolajczyk , M. , Grzejszczak , S. , Zatorski , A. and Mlotkowska , B. 1976 . Tetrahedron Lett. , : 2731
  • Kruse , G. C. , Broekhof , N. L. J. , Wijsman , A. and Van der Gen , A. 1977 . Tetrahedron Lett. , : 885
  • Mikolajczyk , M. , Grzejszczak , S. , Zatorski , A. , Mlotkowska , B. , Gross , H. and Costisella , B. 1978 . Tetrahedron , 34 : 3810
  • Juaristi , E. , Gordillo , B. and Valle , L. 1986 . Tetrahedron , 42 : 1963
  • Seebach , D. , Kilb , M. and Grobel , B. T. 1973 . Chem. Ber. , 106 : 2277
  • Chauhan , M. S. and Junjappa , H. 1974 . Synthesis , : 880
  • Corey , E. J. and Kozikowski , A. P. 1975 . Tetrahedron Lett. , : 925
  • Blotkowska , B. , Gross , H. , Costisella , B. , Mikolajczyk , M. , Grzejszczak , S. and Zatorski , A. 1977 . J. Prakt. Chem. , 319 : 17
  • Mikolajczyk , M. , Grzejszczak , S. , Chefczynska , A. and Zatorski , A. 1979 . J. Org. Chem. , 44 : 2967
  • Gross , H. , Keitel , I. , Costisella , B. , Mikolajczyk , M. and Midura , W. 1983 . Phosphorus and Sulfur , 16 : 257
  • Kim , T. H. and Oh , D. Y. 1988 . Synthetic Commun. , 18 : 1611
  • Stamos , I. K. 1986 . Tetrahedron Lett. , : 6261
  • Kim , T. H. , Kim , D. Y. and Oh , D. Y. 1987 . Synthetic Commun. , 17 : 755
  • Kim , T. H. and Oh , D. Y. 1985 . Tetrahedron Lett. , : 3479
  • Phenylthio(n-propylthio)methanephosphonate: 1H NMR (CDCl3) 0.97(3H, t), 1.37(6H, t), 1.67(2H, m), 2.83), 4.05(1H, d), 4.18(4H, dq), 7.25–7,67(5H, m); IR(CDCl3) 3075, 2998(s), 1260(P=O,s), 1050–1035(vs), 965; Mass(m/e, %) 89(100), 127(47.3), 169(40.9), 225(65.4), 260(79.0), 334(M+ 5.8).
  • Isopropylthio(phenylthio)methanephosphonate: 1H NMR(CDCl3) 1.30(6H, d), 1.33(6H, t), 3.37(1H, m), 4.13(1H, d), 4.17(4H, dq), 7.23–7.50(5H, m); IR(CDCl3) 3080, 3000, 1265(P=O, s), 1055–1030(vs), 970; Mass(m/e, %) 127(66.4), 155(74.5), 183(100), 225(49.3), 260(42.2), 334(M+, 2.3).
  • Isobutylthio(phenylthio)methanephosphonate: 1H NMR(CDCl3) 0.93(6H, d), 1.30(6H, t), 1.67(1H, m), 2.70(2H, d), 4.10(1H, d), 4.25(4H, dq), 7.17–7.67(5H, m); IR(CDCl3) 3070, 2975, 1269(P=O, s), 1055–1030(vs), 965.
  • Bisphenylthiomethanephosphonate: 1 H NMR (CDCl3) 1.27(6H, t), 4.13(4H, dq), 4.40(1H, d), 7.10–7.50(10H, m); IR(CDCl3) 3070, 3000, 1260(P=O, s), 1050–1025(vs), 970.
  • Benzylthio(phenylthio)methanephosphonate: 1H NMR (CDCl3) 1.28(6H, t), 3.93(1H, d), 3.97(2H, s), 4.20(4H, dq), 7.22(10H, bs); IR(CDCl3) 3070, 2990, 1260(P=O, s), 1050–1025(vs), 965; Mass(m/e, %) 91(100), 260(53.3), 382(M+, 0.52).
  • Mikolajczyk , M. and Zatorski , A. 1973 . Synthesis , : 669

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