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Original Articles

STRUCTURE AND REACTIVITY OF CYCLIC ENEDIOL N-PHOSPHORYLAZOLES AND N-PHOSPHORYLTETRAMETHYLGUANIDINE

, , , &
Pages 279-299 | Received 27 Feb 1984, Accepted 06 Apr 1984, Published online: 19 Dec 2006

References

  • Department of Chemistry, State University of New York: (b) Department of Chemistry, Brookhaven National Laboratory
  • Department of Chemistry , Portland, Maine : University of Southern Maine . 04103
  • Ramirez , F. , Okazaki , H. and Marecek , J. F. 1977 . Tetrahedron Lett. , 2927
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  • Ramirez , F. , Okazaki , H. , Marecek , J. F. and Tsuboi , H. 1976 . Synthesis , 819
  • Ramirez , F. , Marecek , J. F. and Okazaki , H. 1976 . J. Am. Chem. Soc. , 98 : 5310
  • Ramirez , F. , Ricci , J. S. Jr. , Okazaki , H. , Tasaka , K. and Marecek , J. F. 1978 . J. Org. Chem. , 43 : 3635
  • Abbreviations: CEP = 1,2-dimethylethenylenedioxyphosphoryl; TMG = tetramethylguanidine.
  • McEwen , W. E. 1965 . Top. Phosphorus Chem. , 2 : 1
  • McEwen , W. E. and Berlin , K. D. , eds. 1975 . Organophosphorus Stereochemistry , Vol. I. II , Hutchinson and Ross, Straudsburg, PA. : Dowden .
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  • Gillespie , P. , Hoffman , P. , Klusacek , H. , Marquarding , D. , Pfohl , S. , Ramirez , F. , Tsolis , E. A. and Ugi , I. 1971 . Angew. Chem. Ind. Ed. Engl. , 10 : 687 cf. p. 694
  • Ramirez , F. and Ugi , I. 1974 . Bull. Soc. Chim. France , : 453
  • Trippett , S. 1976 . Phosphorus and Sulfur , 1 : 89
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  • Hudson , R. F. and Verkade , J. G. 1975 . Tetrahedron Letters , 37 : 323
  • Berry , R. S. 1960 . J. Chem. Phys. , 32 : 933 For the pseudorotation mechanism to achieve permutational isomerization see
  • Ugi , I. , Ramirez , F. , Marquarding , D. , Klusacek , H. and Gillespie , P. 1971 . Acc. Chem. Res. , 4 : 288 For the turnstile rotation mechanism to achieve permutational isomerization see
  • Ugi , I. and Ramirez , F. 1972 . Chemistry in Britain , 8 : 198
  • Ramirez , F. , Marecek , J. F. , Tsuboi , H. and Okazaki , H. 1977 . J. Org. Chem. , 42 : 771
  • Ramirez , F. , Marecek , J. F. , Tsuboi , H. , Okazaki , H. and Nowakowski , M. 1976 . Phosphorus , 6 : 215
  • Ramirez , F. and Marecek , J. F. 1976 . Tetrahedron Lett. , 3791
  • Sarma , R. , Ramirez , F. , McKeever , B. , Marecek , J. F. and Prasad , V. A. V. 1979 . Phosphorus and Sulfur , 5 : 323 For literature on this topic see
  • Ramirez , F. and Marecek , J. F. 1977 . Tetrahedron Lett. , 967
  • Ramirez , F. 1970 . Bull. Soc. Chim. Fr. , 3491
  • Pauling , L. 1960 . The Nature of the Chemical Bond, , 3d ed. , Ithaca. NY : Cornell University Press .
  • Cruickshank , D. W. J. 1961 . J. Chem. Soc. , 5486
  • Ramirez , F. , Lee , S. , Stern , P. , Ugi , I. and Gillespie , P. 1974 . Phosphorus , 4 : 21
  • Ramirez , F. and Marecek , J. F. 1981 . Organophosphorus Chemistry, Royal Society of Chemistry (London) , 12 : 142 cf. pp. 160, 162.
  • Ramirez , F. , Marecek , J. F. , Tsuboi , H. and Chaw , Y. F. 1978 . Phosphorus and Sulfur , 4 : 325
  • Lumme , P. and Pitkänen , I. 1974 . Acta Chem. Scand. , A28 : 1106
  • Sokolva , M. M. , Ostrovakii , V. A. , Koldobskii , G. I. , Melnikov , V. V. and Gidaspov , B. V. 1974 . Zh. Obsch. Khim. , 10 : 1985
  • The reactions of CEP-pyrrole with alcohols may be more complex than indicated here. While there is no question that the uncatalyzed and imidazole catalyzed reactions proceed with exclusive ring-opening, preliminary experiments indicate that the same reactions when catalyzed by triethylamine, quinuclidine, or salts of acetate or p-nitrophenoxide anions seem to yield either products of ring-opening, ring-retention or both of these in a manner which is not altogether clear at present.
  • Macomber , R. S. 1983 . J. Am. Chem. Soc. , 105 : 4386
  • Only three-fold, or larger, differences between the catalyzed and uncatalyzed reactions are considered significant in the present work.
  • Ramirez , F. and Marecek , J. F. 1978 . Acc. Chem. Res. , 11 : 239
  • Ramirez , F. , Tsuboi , H. , Okazaki , H. and Marecek , J. F. 1982 . Tetrahedron Letters , 23 : 5375
  • Ramirez , F. , Gavin , T. E. , Mandal , S. B. , Kelkar , S. V. and Marecek , J. F. 1983 . Tetrahedron , 39 : 2157

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