Conversion of carbonimidodithioates to carbamates

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Mariappan Anbazhagan, T. Indrasena Reddy and Srinivasachari Rajappa


Abstract

Carbonimidodithioates derived from primary amines or α-amino acid esters have been converted to N-benzyloxycarbonyl derivatives under mild conditions by treatment first with sodium benzyl alcoholate and then with water. N-Benzyloxycarbonyl α-amino acids have been generated from the methyl esters by alkaline hydrolysis or from the allyl esters by Pd0-catalysed de-allylation.


References

  1. S. K. Tandel, S. Rajappa and S. V. Pansare, Tetrahedron, 1993, 49, 7479 CrossRef CAS.
  2. T. I. Reddy, B. M. Bhawal and S. Rajappa, Tetrahedron Lett., 1992, 33, 2857 CrossRef CAS; T. I. Reddy, Ph.D. Thesis, University of Poona, Pune, India, 1992.
  3. G. H. Kulkarni, R. H. Naik, S. K. Tandel and S. Rajappa, Tetrahedron, 1991, 47, 1249 CrossRef CAS.
  4. S. R. Deshpande, A. P. Likhite and S. Rajappa, Tetrahedron, 1994, 50, 10 367 CrossRef CAS.
  5. In our earlier communication, 2we have not reported entry 6c. Zeolite HY- or H-Mordenite-catalysed hydrolysis of N-butylcarbon-imidodithioic acid dimethyl ester 6c led to the corresponding N-butyl S-methyl thiocarbamate 7c in 45 or 47% yield, respectively.
  6. H. Kunz and H. Waldmann, Angew. Chem., Int. Ed. Engl., 1984, 23, 71 CrossRef.
  7. H. Kunz and C. Unverzagt, Angew. Chem., Int. Ed. Engl., 1984, 23, 437 CrossRef.
  8. J. P. Genet, E. Blart, M. Savignac, S. Lemeune and J.-M. Paris, Tetrahedron Lett., 1993, 34, 4189 CrossRef CAS.
  9. J. P. Genet, E. Blart, M. Savignac, S. Lemeune, S. Lemaire-Audoire, J.-M. Paris and J.-M. Bernard, Tetrahedron, 1994, 50, 497 CrossRef CAS.
  10. S. Lemaire-Audoire, M. Savignac, E. Blart, G. Pourcelot and J. P. Genet, Tetrahedron Lett., 1994, 35, 8783 CrossRef CAS.
  11. H. Waldmann and H. Kunz, Liebigs Ann. Chem., 1983, 1712 Search PubMed.
  12. D. Hoppe and L. Beckmann, Liebigs Ann. Chem., 1979, 2066 Search PubMed.
  13. T. I. Reddy, B. M. Bhawal and S. Rajappa, Tetrahedron, 1993, 49, 2101 CrossRef CAS.
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