Russian Chemical Bulletin

, Volume 46, Issue 4, pp 832–833 | Cite as

An unexpected pathway of the reaction of lithiated 1,1-dimethylallene with isopropyl isothiocyanate

  • L. Brandsma
  • N. A. Nedolya
  • A. C. T. H. M. van der Kerk
  • W. Heerma
  • E. T. H. G. Lutz
  • R. -J. de Lang
  • A. V. Afonin
  • B. A. Trofimov
Brief Communications

Abstract

The reaction of lithiated 1,1-dimethylallene with isopropyl isothiocyanate gives 3a,4,5,5a-tetrahydro-4,4,5a-trimethyl-2-methylthio-3H-cyclobuta[b]pyrrole resulting from cyclization of the intermediate 2,7-dimethyl-4-methylthio-3-azaocta-2,4,6-triene.

Key words

isopropyl isothiocyanate 1,1-dimethylallene butyllithium lithiation alkylation azatrienes 3a,4,5,5a-tetrahydro-4,4,5a-trimethyl-2-methylthio-3H-cyclobuta[b]pyrrole 

References

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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • L. Brandsma
    • 1
  • N. A. Nedolya
    • 2
  • A. C. T. H. M. van der Kerk
    • 3
  • W. Heerma
    • 3
  • E. T. H. G. Lutz
    • 4
  • R. -J. de Lang
    • 1
  • A. V. Afonin
    • 2
  • B. A. Trofimov
    • 2
  1. 1.Preparative Organic Chemistry DepartmentUtrecht UniversityUtrechtThe Netherlands
  2. 2.Irkutsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesIrkutskRussian Federation
  3. 3.Department of Mass SpectrometryUtrecht UniversityUtrechtThe Netherlands
  4. 4.Department of IR SpectroscopyUtrecht UniversityUtrechtThe Netherlands

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