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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 7
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Original Articles

Synthesis of N-Unsubstituted α-Alkylated Pyrrol-2-Acetonitriles

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Pages 863-875 | Published online: 05 Dec 2006

References

  • Contribution No. 734 from the Syntex Institute of Organic Chemistry
  • 1985–1986 . Syntex Research Post-doctoral Fellow
  • Herz , W. and Toggweiler . 1964 . U. J. Org. Chera. , 29 : 213
  • Zaharieva , K. , Stefanovsky , J. N. and Pojarlieff , I. G. 1971 . Tetrahedron Letters. , : 1663 The pKa of pyrrole is 17.5[Yagil. G. Tetrahedron. (1967). 23, 2855] and that of phenylacetonitrile is reported to be 18 or 20.8 depending on the mode of measurement
  • Greenhouse , R. , Ramirez , C. and Muchowski , J. M. 1985 . J. Org. Chem. , 50 : 2961
  • Muchowski , J. M. and Scheller , M. E. 1987 . Tetrahedron Letters. , : 28
  • Jones , R. A. and Bean , G. P. 1977 . The Chemistry of Pyrroles , 360 London : Academic Press .
  • 426 – 428 . Ref. 7
  • The addition of ethereal ethylmagnesium bromide to (2) gave a 3:1 mixture of (3. R = Et) and the reduction product (3. R = H
  • Carpio , H. , Galeazzi , E. , Greenhouse , R. , Guzman , A. , Velarde , E. , Antonio , Y. , Franco , F. , Leon , A. , Perez , V. , Salas , R. , Valdes , D. , Ackrell , J. , Cho , D. , Gallegra , P. , Halpern , O. , Koehler , R. , Maddox , M. L. , Muchowski , J. M. , Prince , A. , Tegg , D. , Thurber , T. C. , Van Horn , A. R. and Wren , D. 1982 . Can. J. Chem. , 60 : 2295
  • Eyley , S. C. , Giles , R. G. and Heaney , H. 1985 . Tetrahedron Letters. , 26 : 4649 Raines, S., and Kovacs, C. A. J. Heterocyclic Chem. (1970), 1, 223
  • Herz , W. 1953 . J. Am. Chem. Soc. , 75 : 483

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