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DOI: 10.1039/A904680A (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2237-2241

Conversion of N-alkyldiisopropylamines into N,N-bis(5-chloro-3-oxo[1,2]dithiol-4-yl)amines

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Susana Barriga, Lidia S. Konstantinova, Carlos F. Marcos, Oleg A. Rakitin, Charles W. Rees, Tomás Torroba, Andrew J. P. White and David J. Williams

Abstract

Triisopropylamine 1a and S2Cl2, in the presence of DABCO and formic acid, give the bicyclic amine 2a, and its N-dealkylated product 3, rather than the tricyclic bisdithiolothiazine system 7 produced by Hünig’s base 1b. However, when S2Cl2 is in molar excess over DABCO, Hünig’s base and related N-alkyldiisopropylamines 1c–g also give the analogous bicyclic compounds 2b–g together with the tricyclic compounds 7b–g. The N-benzyl compound 2c is debenzylated quantitatively to the secondary amine 3 by sulfuric acid. X-Ray crystallography of N,N-bis(dithiolyl)ethylamine 2b shows the two dithiole rings to be steeply inclined to each other (85°) and the geometry at nitrogen to be slightly pyramidal. The crystal packing is dominated by S[hair space][hair space]· · ·[hair space][hair space]O electrostatic and weak C[double bond, length half m-dash]O[hair space][hair space]· · ·[hair space][hair space]Cl charge-transfer interactions.

References

  1. C. F. Marcos, C. Polo, O. A. Rakitin, C. W. Rees and T. Torroba, Angew. Chem., Int. Ed. Engl., 1997, 36, 281 CrossRef CAS.
  2. C. F. Marcos, C. Polo, O. A. Rakitin, C. W. Rees and T. Torroba, Chem. Commun., 1997, 879 RSC.
  3. C. F. Marcos, O. A. Rakitin, C. W. Rees, L. I. Souvorova, T. Torroba, A. J. P. White and D. J. Williams, Chem. Commun., 1998, 453 RSC.
  4. C. W. Rees, A. J. P. White, D. J. Williams, O. A. Rakitin, C. F. Marcos, C. Polo and T. Torroba, J. Org. Chem., 1998, 63, 2189 CrossRef CAS.
  5. C. F. Marcos, O. A. Rakitin, C. W. Rees, T. Torroba, A. J. P. White and D. J. Williams, Chem. Commun., 1999, 29 RSC.
  6. H. Bock, I. Goebel, Z. Havlas, S. Liedle and H. Oberhammer, Angew. Chem., Int. Ed. Engl., 1991, 30, 187 CrossRef.
  7. SHELXTL PC, version 5.03, Siemens Analytical X-Ray Instruments, Inc., Madison, WI, 1994.
  8. C. W. Rees, A. J. P. White, D. J. Williams, O. A. Rakitin, L. S. Konstantinova, C. F. Marcos and T. Torroba, J. Org. Chem., 1999, 64, 5010 CrossRef CAS.
  9. D. M. McKinnon, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, 1996, vol. 3, p. 569 Search PubMed.
  10. R. F. C. Brown and I. D. Rae, Aust. J. Chem., 1964, 17, 447 CAS.
  11. C. H. Wei, Acta Crystallogr., Sect. C, 1985, 41, 1525 CrossRef.
  12. P. K. Morgensen, O. Simonsen, C. E. Wainwright and A. E. Underhill, Acta Crystallogr., Sect. C, 1991, 47, 1905 CrossRef.
  13. B. Rees, Acta Crystallogr., 1970, B26, 1304.
  14. S. Furberg and J. Solbakk, Acta Chem. Scand., Ser. A, 1974, 28, 435 CAS.
  15. O. Hassel and C. Rømming, Quart. Rev., 1962, 16, 1 Search PubMed.
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